I bought a "fixer upper" not realizing how much it would cost to "fix her up". Do I regret it? No, not at all. It's been six years and I still have a few more projects to do, one of which should be done in the next 6 months. I accept that I wont' recoup my total renovation investment but everything I did was necessary. I didn't over-improve the place, I updated it (which it sorely needed). I love where I live in terms of the overall community, my neighbors and the quality of life. I suppose I could have purchased a plot of land and had a home built but it honestly didn't occur to me at the time. I made the right decision for me.
Deb, best of luck with whatever you're considering.