>Or does he think that less software overall, and less free software in particular, is favorable to more free software existing and also some proprietary software.
You can create proprietary software _with_ GCC just fine, and he has never proposed any measures with which to impose any restrictions on the final output binaries you create with GCC so I don't really follow your reasoning.
The 'problem' with LLVM from his view is that it is easy to incorporate into proprietary software, as well as easy to use in conjunction with proprietary software (through plugins for instance), which means that there is potentially much less incentive to contribute your code back when it's easy to maintain it in proprietary form, which then leads to less 'free' software.
His cynicism has a tendency to come true, so it will be interesting to see if LLVM open source development will continue to flourish or if we will see a slow but steady transition of 'real improvements' happening in proprietary plugins or forked versions rather than contributed back to the open source project.
In some ways we might be seeing it already, last time I heard (which was in september IIRC), Apple had not contributed their A7 support to the open source versions of Clang/LLVM, and are instead keeping it proprietary and only available on the Clang/LLVM versions they ship with XCode on their OSX platform.