Our home is/was a bit of a fixer-upper, and it's harder to get help with labor here (it exists, but it's expensive). But one thing I've noticed is that learning plumbing/construction/mechanics has been way easier than learning software. You definitely sweat more though.
Turn-key housing here exists too, it just comes at more of a premium. Also, your social life is obviously impacted. You're probably well-advised to already have a family or s/o (or just are comfortable being alone).
All told, I think this is a great option if you're feeling trapped in your career but have stockpiled some cash. It probably doesn't require near as much money as you might think to make the jump.
For us it's exactly what we needed to focus on our startups without going the traditional VC route. We'd love to see more people going this route. Let me know if I can help.