awesomeocalypse, I'm going to pick on you because you write long posts and I like people who write long and meaty posts. Please understand that the following is nothing personal, but that I feel that on one hand you are representative of a type and on the other hand clearly intelligent enough to defend yourself as a worthy opponent.
Alignment was a clunky and often nonsensical behavioral straightjacket for players...That doesn't mean I don't lend morality any weight in-game. I just do so in a more organic and interesting way.
One thing that I find annoying about people who decry alignment as an absolute and objective straight jacket is that they tend do so in such absolutist and objectivist terms without providing the slightest bit of evidence or even much in the way of proof that they even understand what alignment is. In fact, I'm often impressed with how little they are able to express exactly what it is that they mean by ethics and morality in general.
Take a look at artifacts for instance. In previous editions, they were explicitly linked to a certain alignment. But in 4e they just have personalities, which have goals much more specific and interesting than merely being "aligned",
The problem with this is that in previous editions, these artifacts might also have had goals and personalities and in fact frequently - when these artifacts were described in any detail - did indeed have goals and personalities. Having an alignment does nothing to prevent one from having a goal or a personality, but having an alignment tells us something about a personality that we might not otherwise now. Take such goals as "Bringing lawbreakers to justice" or of "Protecting the innocent". Such goals tells us little of whether we are dealing with Superman, Batman, Rorshach, or The Punisher. We only may tell the difference when we begin to talk about different ethical values which underly the various persons, and eventually if we systemize those goals to any degree we are going to come up with some sort of 'alignment system'. The system we choose might not be the two axis system of classic D&D, but it will be a system.
May I suggest that one possible crux of the matter is whether or not you believe ethics and morals can be described in a systematic way at all. Let's return to that in a bit.
An artifact might be a relic of a people wholly devoted to trade and commerce, and would reward its bearer for engaging in trade, but punish them if they merely hoarded all of their possessions or if they used thievery to bypass honest commerce. IMO thats a much more interesting approach to introducing some sort of moral standard into the game than merely declaring an item "good" and saying it will only work with "good" people. What does good mean, anyway?
Let me also suggest that that is another possible crux of the matter. One of the biggest problems in any systematic description of ethics or morality is that people will tend to disagree over what actions belong in the bucket we want to label 'good' and the bucket we want to label 'evil'. I've never really seen this as a huge problem, but I can see why some people find it a stumbling block. For me, so long as the world's owner describes what belongs in each bucket for his world, it doesn't bother me that his conception of what belongs in each bucket does not correspond to my personal real world ethics and beliefs. For others, it matters very much to them that there character not only acts in the way that they call good (or evil if they prefer) but that they recieve the label that they think that they deserve for those actions. For my part, it only matters that I'm warned ahead of time what to expect.
Does an orc shaman who has spent his life healing those of his tribe think of himself as "evil"?
Leaving aside the specific example for which we have insufficient information to make an answer of any sort, here is another possible difficulty. I can put it no more plainly than saying, "Does it matter what you think of your own actions?" Surely very very few people indeed think ill of themselves, but what does that matter? Surely far more people do evil than like to think of themselves as evil. Surely evil can feel it has the best of motives.
A specific artifact or person or god might have an idea of what is good, but there is no universal absolute, which is the way it should be.
Once again, we reach a point where a value judgment is being made. We are told that there being no univeral absolute is, 'the way it should be'.
But those godly teachings are never so broad and simplistic as merely being "lawful good" or "chaotic evil". Instead, each god has highly specific goals and things they care about.
But again, in earlier additions of D&D no diety when described ever had such broad and simplistic teachings nor lacked for highly specific goals or particular things that they cared about. Why this pretence that such things were lacking in earlier editions and are novel when introduced?
But in a recent campaign, one of our adventures involved a lord whose daughter had fled an impending marriage to be with her true love, a member of a rival nation. The lord asked us to get her back, but when we reached her, she offered us a different reward to help her and her beloved flee. A few in our party were all for helping her escape to be with the one she loved...but not our Paladin of Bahumut. He figured that Bahumut values order over mere passion and emotion, and would never approve of forsaking a promise like a betrothal in order to follow the whims of one's heart--the noble thing to do would be to suck it up and try one's best to fulfill the promise even if it made one unhappy. We ended up hauling her back kicking and screaming. On the old alignment scale, this might have prompted a long argument over which course of action was the closest to "lawful good" behavior. But in this game, that wasn't relevant, only one god's particular interpretation of "good", which didn't necessarily conform to our modern conceptions.
I fail to see how this was any different than an older edition of D&D except that you've perhaps gotten mature enough not to argue about it in a meta-game way. Valuing order, duty, responsibility, obedience to family and so forth over passion and emotion is a description of 'lawful' over 'chaotic' broadly accepted by virtually everyone that has ever taken a stab at describing the goals of the two competing ideologies. Why in the world should we think this a conflict over what 'good' is, I cannot tell except to say that perhaps the problem is that 'modern conceptions' of good are perhaps biased to one side of the lawful/chaotic question. After all, we no longer believe in the goodness of arranged marriages nor do we think that a parent forbidding one to marry should have the slightest constraint on someone's actions, yet I think on reflection that we would not want to condemn a society that thought that way (say modern South Korea) as being intrinsicly 'evil' for thinking that.
This is, in my mind, a far superior approach to handling moral questions than a built in "objective" system.
Leaving aside the fact that I don't think you've actually discovered a new approach compared to the older system of handling moral questions, note again the bias towards 'objective' systems.
A classic example of the murkiness/overall uselessness of alignment is to try to place most American presidents on an alignment scale.
Before we look at your puzzle, I'd like to note that the real murkiness and uselessness of this sort of question is related to a problem not found within roleplaying games - the incompleteness of information possessed by the persons seeking to answer the question. The major reason IMO we have difficulties answering the question, "What alignment is Batman?" or "What alignment is JFK?" is that every answerer tends to have a different incomplete picture of the character or person who is being put to the test. In the case of 'What alignment is Batman', almost everyone knows who Batman is generally, and is acquainted perhaps with one or three or ten of his adventures, but few of us are so well read as to be acquainted with all of his adventures. You can always tell those that have something approaching expertise in the subject when they answer, "Which one?", because Batman's presentation has evolved and forked in some many miriad ways that we can't realistically call him one consistant character. And, even if we were the expert on Batman, we should never really know all about Batman from the pages of his adventures. The problem with JFK is even more acute, for even if we were a world reknowned expert on JFK, we should know him less well for all that than the average fan boy knows Batman because JFK remains an enigma to history shrouded in secrecy, debate, legend, and mystery, but most of all because we have no real window into JFK's private mental life. There is no definitive account of anyone's life which we may be privy to.
But for all of that, your puzzle is interesting for an entirely different reason than the intended one:
For example, JFK: on the one hand a war hero who bravely risked his own life to save others
What does that have to do with alignment at all? Surely we'd have to know why he did it to say anything about his alignment?
a champion of the poor and downtrodden who laid the groundwork for the Civil Rights act
Again, what does that have to do with alignment at all? Surely we'd have to know why he did it to say anything about his alignment, and surely it is particularly murky knowing the real motive behind the public good acts of a public politician whose success rests on acheiving a certain effect and reputation with the public.
an inspiring and charismatic speaker who far more than anyone else of his generation clearly articulated the ideals by which a modern America should live and act
Again, what does that have to do with alignment at all? This is perhaps the shoddiest evidence of the bunch, because why in the world should be believe being charismatic or inspiring or idealistic is attached to any one alignment at all. It would be like saying, "Which alignment was JFK, well to begin with, he was handsome..." or judging someone's alignment by their atheleticism. It shows in my opinion an utter failure to even consider what alignment means to even provide such as 'evidence' of the murkiness of alignment, which is what makes it so irritating to see it dismissed out of hand and with such an air of self-assurance.
and a shrewd negotiator who helped to avert disaster during the Cuban Missille crisis.
And again, leaving aside that you've just passed a judgment on a very contriversial period of history that would not be universally agreed with, what does shrewdness have to do with alignment?
On the other: a rampant philanderer who, despite his ostensible support for both Catholicism and women's rights, made no discernible effort to keep to his marriage vows
At last you finally provide somthing that most people would consider has something to do with alignment, and here we can finally pass something like an ethical judgment. Either the man found a great deal of difficulty doing what he professed to believe, or as seems more likely whatever else can be said about him, he wasn't "lawful" since he didn't actually follow the external code of laws (Catholicism in this case) he professed to believe. (Hopefully we can mostly agree that Catholicism is 'lawful', and I leave it as uninteresting to this debate whether you find it 'good' or 'evil' or 'neither'.)
a pampered rich kid who used his father's gangster connections to vote the cemetaries in Chicago, thus stealing a presidential election
Once again you've pronounced judgement over an episode of history which even historians would disagree over, but leaving aside that we again find some evidence that either JFK had extreme difficulty living up to yet another aspect of his professed external ethical code (in this case American Law), or else whatever else we may say about him, he is not Lawful.
and a naive and arrogant commander who approved a cockamamie scheme to use the CIA to overthrow the Cuban government, resulting in thousands upon thousands of deaths.
Let me make one other point about this historical snippet: not only did he approve the scheme, but, at the point of implementing it, he had second thoughts and renigged upon his promises to those who he'd caught up in the scheme, resulting just as you say in thousands upon thousands of deaths. So, whatever we may say about JFK, we can be sure that he did not highly value his word or duties he'd imposed upon himself even if it meant leaving those people who trusted him to their deaths, and once again this suggests someone who is not lawful as it is commonly understood. Now, note that I'm not suggesting here that it wasn't the 'right' decision, nor am I passing any judgement on him. For all you know of me personally, I might be an evil fiend that respects a person more for sending people to their deaths and believes that treachery and murder are the marks of what is truly good. I'm merely stating that JFK's actions in the light of the commonly understood meaning of the bucket labeled 'lawful' don't seem to fit in it. And, further that if in fact JFK was in that bucket, it suggests someone who had the hardest time following the precepts he actually believed in. It is therefore much easier for me to believe he didn't actually believe those precepts strongly, and had some deeper real motivations and goals which we might could tease out if we had fuller knowledge of JFK.
Do his successes make him good, or do his failings make him evil
What in the world does success or failure have to do with alignment?
That seems oddly unfocused for a man with such a distinct ideology.
Distinct ideology? Could you say what in the world it is, because I haven't a clue. Which is in fact the problem with abandoning a systematic description, because having abandoned it, we are left with the need to provide a description anyway and doing that is no easier than providing a systematic description in the first place. I mean really, can we conclude what JFK's real goals were with any more precision and general agreement than we can conclude what alignment he had?
Life is not a morality play.
But, there is nothing that prevents a fantasy role playing game from being one. And in particular, even if you fantasy RPG is nothing like 'Disneyesque moral paragons running around killing Nazi Demon serial killers', it's going to probably be a morality play of a sort it just may have very different meanings than some other morality play. After all, a play which means, "Good is relative and the truth is murky.", is still a morality play. And even more importantly, unlike real life, in an RPG we never ever lack perfect information about the characters within. The DM has perfect knowledge of every NPC. He knows their innermost thoughts and convictions. He never has to doubt what there goals, motives, and beliefs are. Likewise, the player has perfect knowledge of the PC. So why should we find ourselves in any difficulty comparable to knowing the alignment of a real person?
In my campaigns, nearly every being with more than a basic level of intelligence has a motivation--and that motivation is hardly ever that they want to be "good" or "evil".
Doesn't it strike you that this is a ridiculous statement? Since when did being 'good' or 'evil' deprive one of motivations?
I'm not interested in a guard who mindlessly attacks the pcs because he's on the evil side
Your strawman is so thin that I wonder you can even make a scarecrow of it.
I'm not interested in the impecabbly virtuous cleric who heals the pcs because its the good thing to do, I'm interested in the cleric who seems impecabbly virtuous, but also relentlessly pursues political power for her church and so extracts certain favors for healing--which of course to her is a "good" action, because she believes her god to be good. I'm not interested in a "good" nation at war with an "evil" empire, I'm interested in two competing countries, each with some legitimate grievances and made up of many diverse people, good and bad. I'm less interested in easy moral "questions" like "should we kill the evil guy?" with clearcut answers like "hell yes", than I am in posing legitimate dilemnas like, "should we help out these settlers in wiping out the orcs who've been raiding their village, even though the settlers themselves drove the orc from their ancestral homeland to make their village?"
None of the questions that you pose are in any way hampered by the alignment system or get less tricky if you have an alignment system. What I'm interested in is precisely the selective bias you state in what you are interested in. To be frank, you repeatedly have staked out a position at every turn which is relatively easy to describe in D&D alignment terms. Whatever else may be said of your beliefs about how RPG's ought to be played, they aren't 'lawful'. You repeatedly describe 'truth' in terms of ambiguity and disorder:
Objective notions of good and evil stike me as being inherantly and by definition melodramatic.
True drama, as opposed to melodrama, is to be found in shades of gray
in ambiguous conflict without a clear resolution.
I love using D&D, and other roleplaying games, to ask and explore moral questions. But those moral debates are only meaningful if they take place on the same terms as it takes place in life--i.e. without objective answers.
Is that an objective truth?
That is, in life we don't have any access to objective answers. None of us do.
Which is an ethical conviction that says more about how you approach life than it does state anything certain about the world we find ourselves in.
Using D&D to explore moral questions is awesome. But they have to be genuine questions. If the answers are right there, bound up in some god's degree, the planar structure of the universe, or an overbearing mechanic, then there are no questions.
Are you sure? Because I'm not at all sure of that, nor am I sure how it follows in your logic. I for my part feel sure that it would perhaps be a different set of questions than the one set that you seem interested in, and I'm not at all sure that the universe is made more complex and interesting when the set of questions brought up by having at least the possibility of objective answers out there bound up in 'some god's decree' or the 'planar structure of the universe' is banished from the universe. In fact, I find it something like two color universe (say sepia and green) where sepia is banned from the universe and all you have to pick from is shades of green. (I'd use black and white, but I don't want to appear to be passing judgment.)
It can be a lovely thing. Look at the recent Battlestar Galatica. It was firmly grounded in high-flying melodramatics (The Chief/Helo/Sharon/Eight, Starbuck and Apollo, Baltar/Six, Adama/Tigh). Would a more realistic approach to drama really served the show any better? 
