I haven't run into upgrade problems with DAW software, but that's only because I don't use DAW software.
Ten years ago when I became interested in recording, I spent a lot of time talking to friends who had set up their own home studios. Most of them had built some kind of computer-based system; every last one of the software-DAW users seemed to be perpetually on the upgrade treadmill, trying desperately to keep their systems operational and stable from one upgrade to the next. I decided back then that I'd stick with self-contained hardware-based recording systems.
I understand the attraction of computer-based recording. The computer is a "magical" machine that can do anything the software tells it to do. New software promises to give your DAW more capability or additional functionality. That's a very attractive proposition.
The problem with this proposition, though, is that a general-purpose computer (hardware and operating system) is not designed to provide an environment in which critical tasks must complete on a hard deadline. (For you software geeks, this is known as a hard real-time system.) It takes all manner of tricks and compromises to make a general-purpose computer process audio without dropping bits on the floor. Those tricks and compromises are fragile in that they rely on assumptions which are easily invalidated by doing things like upgrading the operating system, changing hardware, adding plug-ins or even by something as simple as running another program at the same time as the DAW software.
You can very easily build a software-based DAW that will function consistently for as long as the underlying hardware remains functional. All you have to do is build your system, stabilize it, then never, *ever* change *anything*. But then that kind of defeats the attraction of having a software-based DAW, doesn't it?
I'm not saying that software DAWs are hopeless, either. Given enough technical insight, patience and attention to detail you can certainly operate a robust, stable computer-based DAW while selectively and carefully upgrading your system. If recording is your primary focus, then a computer-based DAW is going to be an indispensable part of your toolkit.
For someone like me, for whom recording is a means to an end, the added complexity and maintenance effort associated with a computer-based DAW is nothing but an unwanted distraction from creating music. The inherent limitations of my recording environment compel me to concentrate on *what* I'm recording rather than *how* I'm recording and processing the tracks.
I personally prefer Mac OS to Windows, but would hesitate to say that switching to a Mac will solve all of your software-DAW problems. You should be somewhat better off if you stick with Logic or Garage Band; presumably Apple pays attention to ensuring that their software upgrades are somewhat synchronized so all of *their* software continues to work together. But you still have the underlying problems of running a DAW on a general-purpose computer, and you still have to be concerned about drivers for third-party hardware.
Again, if you build a system and then *leave it alone* you should be OK; I might go so far as to imply that a Mac-based system *might* be more reliable, on average, than a Windows-based system. But "buy a Mac and you'll never have another problem with your computer-based DAW?"... I certainly wouldn't bet real money on that outcome.