dietsche (./7) :
1) Kevin and Sebastian have done a great job on IDEs, but I'd recommending dropping the IDE. This allows a focus on the tool chain and library and avoids wasted effort. Instead, package something like Eclipse or Anjuta (why reinvent the wheel).
My opinion on this subject is well known (search this forum and the TIGCC message board at TICT HQ, you'll find several reasons why this is a horrible idea, I'm fed up of repeating them), but if the GCC4TI folks want to make their project less useful, it's their choice. (It'd mean that project files would no longer be compatible between the 2 projects though. There's no way TIGCC is going to switch to a third-party IDE.)
2) drop support for old AMS versions; it is easy to upgrade with a link cable or PC. This reduces complexity of the project. It might be pretty safe to pick the very latest versions of the OS. I don't think TI puts much effort into these calculator models anymore, so future OS versions are somewhat unlikely.
The TI-89 and TI-92+ cannot be upgraded beyond AMS 2.09, so that'd be at least 2 "very latest versions" to support. So all the AMS version machinery would still be there and there's not much to gain. It's not that hard to keep backwards compatibility. And in addition, PedroM doesn't implement most AMS 2 or 3 ROM_CALLs either.