I see this getting thrown out a lot, and I've actually been responsible for using it a few times.
The big problem with that argument is not what you (the geek) can do with it's phone, it's what common people do. The success is measured with the sales of the 99% of the people that cannot do that (and it's harder than installing windows - you first have to root the phone, get into recovery, etc etc).
This is where apple shines. If an OS is available, it'll be available for every phone that supports it. Google does the same with the nexus line but big companies don't.
But you got one thing straight. The path for Android's success has to be platform independence for (most of) the OS. Windows works fine on any machine (even macs), Any version of android should run on any Android that follows a certain specification.
For that to happen, standards have to be made. Android should be able to see what hardware was there and download the optimized drivers by itself, for example. But this is all kind of utopic, so... No, I stopped doing anything about it (on my Desire) on 2.3. It's not worth the hassle to get Gingerbread running here.