In the end, I think the ultimate success of a project like this is dependent on two factors
1. Just
how much and
where you'll need to maintain a presence in the Windows landscape.
Simple truth is that transitioning to Linux is not purely a philosophical or political decision. There are practicalities to consider because available technology is also a key factor. If there's something that's Windows-only, you're always going to need to maintain a presence in Bill Gate's world. Same goes if you need to
interface with other people who are exclusively Windows-based users. We are not islands.
If I only had to deal with my own requirements, I could easily move 98% of my computing and online life to Linux and not even blink. What little Windows I'd need to keep would be purely because there will always be apps (that will only run on Windows - or very inefficiently under emulation) I'd be reluctant to live without.
But because I have friends/family who look to me for tech advice and support - and a business that needs to interface with a much larger world - my actual day-to-day split is closer to 60% Nix to 40% Windows. (This ratio varies. But even under "ideal" circumstances, Windows always seems to require at least 15% of my computing space.)
So what does this mean? Simple. When I'm doing my "own thing" I'm almost always doing it exclusively under Linux. When I'm doing everything else, I'm at least 75% Windows no matter what.
I've since learned not to worry about it too much. I'm not into the politics. All I ask is that my
personal systems "do" for me the way I want things done. As long as I've got my personal productivity space working that way, I'm happy.
2. The degree of sheer
bloodymindeness you're willing to bring to the table.
Almost anything can be made to work with a sufficient investment of creativity, time, and hammer bashing. The real question is how much of that is worth it.
I don't know of any hard and fast rule for dealing with that. Once in a while I'll get my nose out of joint about not being able to do something. I'll then invest a ridiculous amount of effort into getting around it. But I've noticed it happens less and less often of late. Maybe it has something to do with me mellowing out a bit. Most likely it's more to do with me maintaining a dual-boot machine as my main desktop.

Hear ye the words of a great sage:
"If at first you don't succeed, try, try again. Then quit. No use being a damn fool about it."
-- W.C. Fields 