The problem with unsupported installs is that they tend to all be special and unique snowflakes – everyone does their own thing their own way, and the person doing the install tends to lack the knowledge and experience to be able to identify the important unique detail in their install (if they could do that, chances are they could also fix the problem, having identified it).
That’s the reason why we’re so quick to mark installs as “unsupported”. It would probably be more accurate to term them “unsupportable”. They’re special and weird, so we have no idea how they’re configured, and they’re run by someone who can’t help us help them. So, since we’ve only got so much time available to help people, we stick to the straight and narrow where we’ve got some hope of being able to figure out what’s going wrong. Even then, people do the damnedest things when following what seems like a straightforward set of instructions, and cause all manner of grief.
(When I say “we”, above, I’m referring not just to CDCK staff, but to the general community of helpful people here on meta)
I’m not sure what you’re planning on actually doing, though, other than encouraging yet more people who lack even the knowledge and experience to figure out how to do an unsupported install by themselves to put themselves in a position where nobody can help them. We really don’t need more encouragement for people to dig themselves a hole they can’t get out of – as you say, there’s enough interest in doing unsupportable installs already.
After a bit of a look, it seems you’re working for Nanobox. That puts a bit of a different complexion on things. My feeling is that you’re not being straight with us here, now, by talking about “unsupported installs” in general, but then pitching your PaaS and not saying up-front “this is where I’m coming from”. That doesn’t sit well with me. It feels like you’re not out to help people with unsupported installs in general, but rather you just want to drum up some business. At the very least, I think you need to fix your topic title and body to be clear about what you’re talking about. It would also behoove you, I think, to spend a bit of time looking at the history of other third-party installs of Discourse, and the amount of annoyance they’ve caused, and have a bit of a think about how you could do better than them. Because $DEITY knows there’s an awful lot of room for improvement there.