I work in finance and frequently talk to people who were bankrupted by having nearly everything invested in real estate.
The two main reasons for this are: Leverage and Timing.
Almost everyone who got burned had bad timing and poor use of leverage. OP shouldn't have either issue.
You're right in that he should have backup plans, cash reserves, and be careful, but I wouldn't worry about his situation too much, personally, especially since he's willing to put in the work. He'll need to keep working to improve it, but that's part of his plan.
These are very good points. I have an old boss. He's unemployed right now. He's gotten laid off many times in his 30+ years in the work force. But he's frugal and has saved enough that he doesn't really care, and usually enjoys 6 - 18 months off between jobs to fix up his homes.
Every time we have lunch, he will recommend ways to reduce my taxes. Example: he has an orchard. People come to pick the fruit and keep them watered and pay them. But he gets to depreciate the property. Another example: a rental home.
I think they are great ideas. But I have 2 young kids and we bought our current (and only) house darned near the peak. I don't feel comfortable with the amount of leverage required to get a second home or property. The difference between when we bought and the bottom of the market in our area was $300k.