I wouldn't buy a fixer-upper unless I enjoyed fixing-upping. Or could pay someone to do it for me. I actually do enjoy it, I love finding out how to do new things, but it's not a hobby and I wouldn't want to spend a lot of time in the future having to fix things rather than go for a swim or go for a ride or sink into the couch with a cup of tea and the cat. I've built a porch once - lots of fun, am never going to do it again because we spent 5 times as long doing it as a carpenter would. I'm all for doing stuff that gives a lot of effect for your time and money, though, like painting. And I'm game for remodeling for a shorter period of time, say 3 months. After that it had better be 5 years until we need to do something drastic.

That said - I think most people are pretty good at adapting to what they get. And if it's a really hard choice, chances are you would be equally happy both places, otherwise it wouldn't be a hard choice. Personally I tend to overestimate what I have and have trouble imagining myself somewhere new. I'm feeling pretty sad about moving out of our rather tiny apartment now because I'm losing a view. But then I tell myself that our next place doesn't have to be the home of a lifetime, just somewhere that I'm reasonably sure that I can thrive for the next few years. The last place wasn't perfect and if I expect the next one to be I'd never find anywhere to live.

Good luck