If you are getting a good deal on a place and it is just a regular-style house, I would run numbers compared to AirDNA and Mashvisor's estimated revenue.

Clear your head and decide what’s your “why” from this point on in life.

I appreciate the heads-up about the saturated multi-family market, that's definitely something to consider. 

You know the area, plus appreciation, you won’t regret having this asset in the long run. 

I currently have a lawn care business that I run myself.   

You can just answer it without the jazz, and I bet you know a few places right off top of head where people WANT to live, right. 

Again, if your $250k is true, and includes all the electrical upgrades, new plumbing runs, potentially new foundation pour (since I assume the existing garage slab is not capable of supporting a new two story house), I am guessing since I don't know the market, but assume you will have a lot of equity by completing the project.

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Otherwise they just run around and bid projects for people that don't close.

Now VRBO is where we are running into a challenge.