1) Non-Essentials
D&D 4e appears to be outdated with the new Essentials (4E) lineup. I don't want to buy errata-filled books which are not even the current rulesets. There are a LOT of D&D 4e books which, while not bad, DOES intimidate me because I cannot read fast and do not have a lot of money (only a lot of Amazon.ca gift cards).
2) Essentials
Now, the problem with this option is that the game has recently gone through several changes with the new Essentials lineup. The players Handbook 1 has 22 pages of Errata. There is a new Essentials rulebook (Rules Compendium). New players handbooks (Heroes of the Fallen Lands and Heroes of the Forgotten Kingdoms). I looked at the Rules Compendium today and it looked well done. However, the Heroes of the Fallen Lands book looked so elementary. Characters had some fluff followed by what seemed to be a limited amount of pre-determined builds. Everything seemed to have limited customization. Now, while players don't consider Essentials 4.5, I cannot see how such rule changes to the game and character development is still 4.0e. Now, I get a "n00b" start to what appears to be a rather complicated game. But if I was intimidated by rules, I would just play World of Warcraft or Guild Wars again. I can then buy some of the pre-Essentials items to round it out or rely on the Character Builder which, while interesting (the demo), seems to limit the immersion I want to get out of the books (I enjoy fluff).
Before you think about whether the rules are up to date are not, and try to ensure that everything in your startup kit is errata-maxed, I think you should consider the potential satisfaction you get from the system. You can get away with playing 4th Edition without errata, so long as everyone at the table is having fun, and the DM is reasonable and capable of resolving problematic points in mechanics.
For example: While there's a significant amount of errata that makes major changes to powers -- Magic Missile, et al -- a larger chunk of errata is really just nitpicking adjustments like rewriting the phraseology of the Stealth rules so that people stop exploiting the wording so they can perform cheese maneuvers. Simply put, the errata is unnecessary if a DM can say, "NO. I don't care how you read the wording, you cannot perform your cheese maneuver since the rule was obviously not intended that way."
Regardless most of the moving parts that are addressed by errata lie in powers and race and class features that are up dated in the character builder. Not that you should feel required to have a DDI subscription, but if you pay for a few months subscription, the broken bits are mostly taken care of for you until the next major set of revisions which frankly, tend to only occur when big changes happen in new supplements.
2) D&D 4 Essentials
TOTAL: $157
3) D&D 4e
TOTAL: $282
I think it's really unnecessary for you to invest in all of these books at once.
So many people (on EnWorld) just say to drop the old 4e stuff and just use the Character Builder and Rules Compendium. That's nice, except I enjoy learning from reading a book. That is a large part of my interest in getting a D&D game.
I completely agree with you. I prefer to learn from a book, even if I run a game using mostly digital tools and pieces of prefab content. I think you should mix it up then. Get a combination of books while using those materials.
My recommendation? Think in terms of needs.
LEARN HOW TO DESIGN: Dungeon Master's Guide 1/Dungeon Master's Kit.
LEARN HOW TO PLAY: Player's Handbook 1/Heroes of the Fallen Lands.
BUILD ANY CHARACTER, REVISED W/ ERRATA: Character Builder (DDI)
USE ANY MONSTER, W/ NEW STAT BLOCK: Adventure Tools (DDI)
I think it's not so necessary to have complete books. 4E is based on a premise of simple baseline rules, broken by multiple exceptions (as given by character abilities). In that sense, the later supplements merely add on complexity and options.
The additional DMG2 adds mechanical options -- as well as more 'fluffy' storytelling techniques -- that can help build a better game, but aren't really crucial if you're a pretty creative person yourself.
The additional PHBs don't really address anything critical to play EXCEPT for the mechanics unique to the classes (i.e. How to use psionics, et al). All the basic rules are in the first PHB
The Monster Manuals have some fluff that helps you make contextual sense of the monsters in the Adventure Tools, but aren't really necessary if you're just a creative person who will make your own monsters or take existing ones and 'reimagine' by renaming their powers and changing their descriptions.
2) What makes D&D 4e feel like World of Warcraft? While having played that game for 1 month, I didn't find it that amazing (it was a good game, just not life-changing). Baldur's Gate II, on the other hand, introduced me to a world of endless opportunities and such (D&D 2 rules). I like customization. I want my character, weak or strong, to be and do the things I want them to. I don't like the long drawn out combat that I hear 4e has. I want tactical combat (I like wargames).
I've never EVER played World of Warcraft, but it's like World of Warcraft in the sense that the characters are designed to work as a team and have clear cut roles in how to do that and combat is a highly tactical affair (and sometimes, a time-consuming one if you don't take measures to avoid it)
That's pretty much where the similarities end, as far as I'm concerned. 4th Edition can seem very videogamey if you take the books at "page value" by throwing your players into one combat after another, and reducing all non-combat situations into a series of lifeless skill checks.
But if you're creative and have a flair for taking these components and making them into a narrative string that is exciting ("We chased the bad guys on a moving train, but then it crashed! And then we had to fight! But then the enemy surrendered, so we had to interrogate him! But it turns out he was a good guy, so we had to investigate and find out who the real traitor was!") then it's nothing like World of Warcraft.
As for customization: there's a lot of that in 4th Edition. You can make a broad range of characters, so long as your players can find creative ways to justify the gamey things they choose, like creating rich backgrounds for why they've built an Elven Swordmage/Artificer or taken a story angle as to why they've inherited the Mark of Warding.
You might miss being able to take skills like "Ride" or "Craft" but those are things a DM handwaves by communicating with his players about what they want their characters to be, rather than requiring them to invest character-building resources in them at the expense of more meaningful tasks like uh, role-playing.