Interesting idea Killersan. That would definitely take the difficulty out for the main audience. Are you sure that you don't want to just encourage people to pick up a cloud subscription in such a case though? If you're going to make it so easy, it makes more sense to have that as a cloud option. I just don't want to lose the ability to completely manage a system on my own for instance, that was the whole idea behind getting an On Premises license. I have my own forest of server machines, and I'd rather not have to wipe the machine each time there was an update.
If it's an option, well then by all means I won't stand in the way, but a full blown reset each time really would be a dampener.
Honestly, I've been with it a while, and in truth the stuff isn't that difficult to keep updated once you know what's going on. The real problem is with documentation, it takes a while to learn what's going on because there's very little written down, and when people do learn it, they keep it to themselves because its not their job to do the upkeep. You could potentially save yourselves the work on pre-packaging solutions if the steps were just a little easier to understand, or written down at all. Or even if you recommended an application like HeidiSQL, instead of having people try to navigate the command-line of mysql when they really don't need it.
I don't know, I'm just blathering on at this point it feels like, but I just wanted to make sure that the advanced users don't get messed up with it as well. On a side note, I don't honestly think this application has really "supported" anything other than Cygwin, which isn't that hostile of a feature. It never really explained things to end users, so people just used whatever worked.