Hi David -- I have never encountered the issue you're describing in my work with osgBullet. But clearly, if you built a project with RTTI disabled, then dynamic_cast would fail. This is true of any project, not just osgBullet.
I'm currently using Bullet 2.80, osgBullet trunk, OSG 2.8.5, and VS 2012. I've built Bullet with double precision enabled and also selected MS CRT DLL. I have 64-bit binaries. It's unlikely I'll have any time in the near future to attempt to reproduce your issue with VS 2010, Bullet 2.79, osgBullet 2.0, and OSG 2.8.3, so you're pretty much on your own for this.
You've mentioned only 'd' Debug executables; is the problem specific to Debug builds?
Are you getting any warnings during link?
You say the problem is related to RTTI, but you didn't mention that you verified the link lines of all three projects to ensure /GR was present (or whatever the option is to enable RTTI in Visual Studio), so that's probably worth checking.