My advice would be to save that cash as much as possible and house hack with the FHA loan and find a community college that you can possibly attend for as cheap as possible to pursue the initial coursework to make sure it's what you want to do. 

@Marcus Auerbach it is the mid west so there are some cheap properties.

In a boom market, investors seem to be able to make money by throwing darts at a board, but how does one do well in a down market.

Eventually you get to enough units where you don't need cash reserves per property but rather one lump sum and for the most part rent from other units pays maintenance on the one that needs a roof. but if you wanted a cheap answer, I'd say save up until you have about enough to replace the roof and stop there.

"You went with him because he was cheap/"investor-friendly" until after you read the post.

Paint is cheap but improves the value by a significant amount. 

It’s an extremely attractive market to someone raised in a market where a cheap home is 250k.

If the numbers you laid out are accurate I would suggest seeking an investment that throws off enough cash flow to also pay for your parents to stay put in their current rental.Having said that, It feels like you have every excuse *to take action but are getting caught up in a lot of what-ifs.

Of course, this means Austin isn't a cheap market anymore, but with the right planning and defined goals, investment opportunities are still available.

There are a lot of options where you can put down 3.5-5% via FHA, not have to spend anything on rehab, AND live cheap.