Wine Compatibility VS Stability

Yes this is both a rant and a general overlook of how and why things work the way they do with the Linux and Wine communities and where things are headed.
First of all I'd like to start off by saying that me and most of my friends think that Ubuntu 8.04 32bit is the most stable and compatible version of Ubuntu ever released. Why do we think this? Well it's because 8.10 and 9.04 just don't seem to play nice in the long run. We don't know why. Some of the packages and features are missing and in 9.04 the button to turn off the computer in Gnome is by the clock instead of on the familiar left side of the screen. General faults and programs crashing are much more evident than in 8.04. Yet if we are forced to upgrade 8.04, it's programs, and their dependencies the OS becomes more unstable. It's very similar to Microsoft's Windows in that if you use Windows XP SP2 it's the best version of Windows Microsoft ever put together but when you start upgrading to SP3 and adding newer components it turns into Vista. For example in Ubuntu 8.04 32 bit it was not only possible but common to install Command and Conqueror 3 Tiberium Wars in Wine and the network play was flawless. Now if you install it you can't use network play after upgrading. PlayOnLinux still supports the patch for online play even though it doesn't effect anything because it no longer works as proof that it once worked. Call of Duty 4 is another example. Once you could run servers that were visible on the internet but now it's almost impossible.
So what do we get in trade for all of this? More hardware support, newer games are supported in wine, and it runs faster. Is it worth it?
Ask yourself this question. If you are a Guitar Hero fan (assume you are) and you play FOF or Frets on Fire on Linux and you notice it only runs properly on 32 bit installs of Linux when you know your computer runs faster with a 64 bit OS what do you choose?
Here is another question. What if you were me? What if you spent hours working on figuring out how to get lets say Call of Duty 4 Modern Warfare servers working properly in Linux and being recognized on the internet. Now imagine that Wine is altered and upgraded and COD4 no longer works properly with network play. Now you see where I'm going with this.
How about Audacity? It use to have a fully working pitch changer (not speed / tempo changer) built into it but in the upgraded version that comes with Ubuntu and is automatically upgraded on older versions, you can't have a pitch changer.
Who decides what to keep and what to leave behind? Why leave anything behind? If something does not work when we upgrade and patch it means that we have broken something. If breaking something makes something else work then we need to find another way.