That's all very interesting. I'm primarily a desktop C++ developer, so I don't run into the headaches of things like VS's database connectivity.
I recommend giving 2010 a go. If I recall correctly, 2010 was the version where they drastically reworked Intellisense. In previous versions, even my moderately-sized projects would break Intellisense upon reaching x lines of code. I don't think the multi-monitor support is any better, though. You can drag documents to their own window on any screen, but I can't seem to group them into sets of tabs.
I'd like to give 2010 a try, and I may at some point here, but everyone else is in 2008 and I'm not sure it'll translate entirely (code has to compile everywhere, and saying ASP is a second-class citizen is insulting to second-class citizens everywhere. I have zero faith it'll work the same way in both versions). I have heard a lot is better in 2010, but in general it's still a Microsoft product; huge, inconsistent, and so tightly bound into everything that they have no proper competition.
Oddly, Intellisense is generally keeping up with me, despite the site being at least a few hundred thousand lines of code (light on the abstraction, though, so it's mostly flat .NET code. Probably not too taxing on intellisense). There are times I just break out Notepad++ and finish up stuff VS was breaking, but it generally catches up any time I build the relevant projects.
And I should be clearer, because it's so weird: the designer-view was actually instantiating the entire window control, as it's init contained the database connecting code, and firing events on the combo box controls that queried the database. At no point was the database actually connected to VS, which you can do; and I'll never even consider trying it, after seeing that happen.
If the intellisense is the complaint, nothing beats the Visual Assist plugin. VS10's intellisense is better than what it used to be but still nowhere near VA.
Also, VS10's WPF-based UI is a nightmare, but that's another discussion...
Finally took a look at Visual Assist, as I've heard about it but never looked at it. That's very impressive. How much does it affect VS's speed on a fairly normal system?
I'd say 'It doesn't', which is objectively impossible but does represent my perception. In 7 or 8 years of using it, I have never found it to be a problem. This is with working on C++ projects with a total size (including third party libraries like boost) of around 400 megabytes of source code. The parsing of code happens behind the scenes; sometimes (when starting VS after a major update from source control or something) you see in the status bar 'Visual Assist: updating databases' or something like that, and sometimes the syntax highlighting takes a few seconds to kick in, but again I've never been annoyed or irritated with delays for which I had any reason to believe that they had anything to do with Visual Assist.
Of course Visual Studio still does its own parsing in the background, for example for the class browser. VA provides something similar, maybe I should use that one and see if there's a way to turn off the Visual Studio Intellisense. It is my subjective impression that this one does sometimes slow down the IDE itself.
My only complaints are the recent price hikes: 249$ -_- ? Those are getting above discretionary purchasing power and although I guess there is some effective productivity gain, it's very hard to quantify and therefore justify... Especially when other people don't want it, because then if you do want it, you look like a wuss who can't hold his own without having his hand held by pretty colors (simplifying of course but let's face it, this is what it looks like from the outside).
I recommend giving 2010 a go. If I recall correctly, 2010 was the version where they drastically reworked Intellisense. In previous versions, even my moderately-sized projects would break Intellisense upon reaching x lines of code. I don't think the multi-monitor support is any better, though. You can drag documents to their own window on any screen, but I can't seem to group them into sets of tabs.