Obviously YMMV, but here are my answers to your questions.
It seems in many cases that unavailable content seems to be by the users more important then available content.
(For instance when you spoke of the compendium, you seemed to indicate the lack of certain content weighed more heavily on whether or not the tool was good.)
See, the whole point of the Compendium is to make it so that
I don't need my books to do adventure design. But if I want the full suite of options available to me, that is no longer true, which makes the Compendium substantially less useful. I used it as a stand-in for my books; it cannot serve that role completely any more. So, yes- the lack of content is what detracts from the value of the Compendium.
Compare it to the SRD for 3e. I know it served a completely different purpose, but I think my analogy will hold. The SRD was a collection of the most basic rules, and while it might be a useful reference tool, it wasn't what I used to design adventures- I used my books instead.
Now the Compendium is sliding towards "useful reference tool" when up to now it has been a "replacement for having the books on hand". Its basic function has changed for me, not just its functionality- and it isn't a function I need or want to pay for.
It also seems people put more weight on the tools- IE if the CB lacks functionality, the system is devalued...
So in this case if the system worked perfectly, could export characters, and maybe had an offline mode, but only had a limited set of books, would this be more valuable?
Absolutely. But since the standard that WotC established with the original CB was so high- really, it was their one shining digital success- anything less than the original's level of performance would still be of lesser valuable than CB1. And part of that level of performance was "all the options at your fingertips!"
I recognize that this sounds unfair, but even an equally-stable, equally-fun CB2 with the same rules support as CB1
but no further updates is a significant loss of value from what we had. Again- the whole point of the CB is to let you avoid having the books on hand. If it's missing a bunch of options, you are back to writing a character sheet by hand. And really, until there is (at least minimal) house rules support in the CB, this is where we're at. In this state, the CB is worthless and useless to me.
Also at what point, would an increase in price feel justified?
If the tools functioned right say, 95% of the time, and DS and Essentials were added to them- Would that warrant an increase in subscription price?
First of all, I agree with the premise that a DDI sub is a great value, assuming that DDI produces anything I'm going to use. As it stands, a good Monster Builder, a good Character Builder
or good content in
at least one of the online mags would probably be enough to convince me to renew at the current price. But to justify an increase, they would have to
quit screwing up the good stuff and
improve things instead of letting them degrade constantly.
So, had they indicated that they were releasing a web based CB that would be released in 2.5 months- would that have made people less upset?
Would more information in your opinion be useful, or add fans to the fire so to speak?
I don't know- but it's the misleading statements that really pissed people off, imho. Leading folks to expect Dark Sun and Essentials in the CB was a bad, bad move- now the "liar liar!!1!!" cries have a lot of sympathy.
If the new CB wasn't ready (which I think is very clear), they should have announced it as a public beta and continued support for the CB1 in the meantime. I know it takes more resources;
I don't care. What WotC has done instead has cost them quite a few subs and garnered a great deal of ill-will for them, as well as shattering what credibility their digital offerings had started to build. I
cannot believe that this is a win for them, nor do I think the sales gained by piracy deterrence are going to make up for the money lost in lost subs and people giving up 4e entirely in frustration.
The irony, of course, is that when most groups do that, they usually move to a different version with no online tools at all. If WotC hadn't established such high expectations pre-release with all their "guaranteed, DDI goes live on release FULL ON!!1!!", I doubt very much whether they'd generate so much anger.