That's precisely the problem I have with a lot of "open source equivalents." They are not targeted at the users that use the original application to the fullest. They're targeted more at the casual users. That's fine, but it's not the same program.
And no, I don't think it would be helpful to contact Microsoft. I've also not contact Mozilla after a few lackluster attempts at getting bugs fixed via bugzilla. This has little to do with the closed/open source aspect and much more about the sheer size of a program. Once it gets past a small development team, it becomes much less useful to seek support and much less likely that the bugs that affect your corner of the use case for the application will be addressed.
The company I've actually had the best support from has been Adobe for Flex. I've found that they are very responsive to bug reports. FAR more responsive than any large scale open source program I've ever used. But the end result of that is a new patch or fixes in a new version. Yes, they give these patches out for free, but that is really just an extension of the large original price that was paid for the original product. I don't personally believe this would work if the majority of the users freeloaded and left the purchasing of support to a small handful of users. Especially for a technology like Flex that's just getting off the ground and isn't already embedded in corporate needs.
And, of course, the really major improvements come out in a new, paid, upgrade.
I really do feel your last paragraph is apples to oranges. You're just talking about moving from one method of selling copyrighted material to another method. A better analogy would be if the VCR and movie rental places came out and it had been perfectly legal to dupe the tapes all they wanted. Do you think it would have become a major source of income? Do you think movie studios would ever have joined in and released their movies on videocassette?