@Austin Pesce Hey man! Great post and great questions. Here's my opinion:
Doing the work yourself always sounds fun and like a great idea, but if a house needs 100k in renovation, it's probably better to hire the whole thing out. Doing the work yourself will take 10x longer. Even if you are a contractor, you can't work on different trades at the same time. You'll be able to learn a ton just by overseeing the project... Speed plays a big role in renovations.
As for the market - nobody has a crystal ball, but I would absolutely have the same concerns. Doesn't mean I wouldn't do the deal, but I would make sure to mitigate the risk as much as possible. I'd be making sure I got a great deal, not just a good one. I'd make sure I'd have enough in reserves. I'd make sure I was buying in the most desirable part of town. I'd be crystal clear on the numbers, my goal for the property, and my exit strategies.
Most importantly, I'd be asking myself what the worst possible outcome could be and how likely that outcome is to happen? If it doesn't seem that bad, or if it's something that you can recover from, then take your shot. If a deal goes sideways, that doesn't mean you fail. You only fail if you were to quit after that bad deal. But if you keep moving forward and eventually become successful, then is that failing?
Best of luck!