If the answer is yes and I'm waiting on other people or uncontrollable aspects, then I turn my focus on the next positive item that I can accomplish.

And it will be a gamble because you can't really answer that question for sure.

That's not to say it it's bad to buy here, but you do have to be picky about what you buy.However, there are greater reasons to invest in SD real estate for a house hack:-Appreciation over cash flow (a gamble, but a fairly safe one over the long term)-reduction of living expenses.  

I would hope to make 25,000 after everything, but i know it is always a little bit of a gamble.

You would be gambling on appreciation, and that is speculation.

Regardless, you took a gamble and it didn't work out.

It's still is a gamble.

It looks like you're now aware you need to go back to the drawing board, so that's good].As for your assessment on the area's potential (vs negative economic possibilities), at the end of the day, you'll have to make your own investing/gambling decisions.

Or throw the dice and gamble the investment will come up roses and pay off the debt.

It's too much like gambling.