My n900 (Dec 09) has never neeed to be flashed, even though I install & use loads of -devel app's on it. How come (am I just a lucky sod?) - nope, it's because I read about stuff which is still in development before I install it. That way I understand:

(a) how stable it currently is (dev's own opinion/caveats; early adopter feedback)
(b) it's functionality (& therfore it's risk level to my phone if buggy)
(c) the correct way to install & run it whilst still under development

oh ... and regarding hard to configure community app's

I think you're putting too much onus on the phone to be smart and too little on yourself.
I admit that most folks want stuff to "just work" these days but the reality is that stuff running on a PC is inherently complex and unless you put some effort into learning the basics you'll not often get the benefit out. It's give a man a fish/give a man a rod here ... I'll take the rod, every time :-)

The N900 will always be best suited for those who like to tinker/learn as well as just "use" their phone. That is (or should be) a prime reason why they bought an open(ish) pocket computer with (adequate) phone capability in the first place, no?