Perhaps I need to up my Google game!

A lot will depend on what type of real estate you want to become involved with; rentals, flips, wholesaling, brrr, singles, multi-family, commercial, etc.Here are a few suggestions:  (especially for singles and small multi-family)  concentrate on the best school district, get the worst house on a great block, stop your car and get our and actually speak to people working on their yard or just sitting on their porch, eat at a local mom/pop coffee shop--sit at the counter and speak to the waitress and customers.  

She looks at things from an investor's perspective, and helped me purchase the duplex that I live in. https://www.realtyaustin.com/agents/Jen-Berbas.phpSince purchase prices and property taxes are pretty high, SFRs in Austin are definitely an appreciation game, not cash flow (assuming the standard 25% down). 

I completely agree with you that 'gambling', or what I prefer to see as calculated risk taking, is certainly part of the game.

Almost like a VRBO except you would bring your own house.On the surface this sounds like it would be reasonable but I would ask how you plan to market the concept to your customers.

If they come here, then it's game on. 

Are you looking for customers?

Thank you James, it wasn’t scaring me away too much but it did have me thinking, but I feel that since I’m so early in this game I’m still dealing with that nervousness and fear at times since that stuff isn’t easy to shake off.

@Rashard Dennis They usually require some skin in the game.

Of course you could also go higher if you are going with very high and, custom finishes.