He is more than capable of paying the rent but is intentionally withholding.

It could be hunting, working Labradors, sports, ocean sailing ships, guy movies, Arnold Schwarzenneger, etc. 

As I sit here planning my goals for the week I am struck with an overwhelming sense of fear, my initial thought is "Am I even capable of pulling this off?".

Don't forget the all-important capability of interfacing seamlessly two ways (reservations and cancellations, reductions in group blocks) when you build it out. 

The average price may be creeping close to $300k but they have an enormous amount of land and capability to build.

Home need quite a bit of cosmetic work, most of which I am capable of doing over time.

So, you have a few options:Take on substantially more challenging projects, both in size/scopeTake on projects that involve a different asset classDeal with challenges related to different geography (I'd think you'd want to move 'up' market)These are the things that you can do one or more of - you may want to think about your options and be realistic too about your capabilities.There's a lot of people doing a lot of different things on these forums, but the above gets you moving 'up' the value chain with regards to developing capabilities, and working towards furthering your 'build' skill-set.All this said, I have a friend that operates in a smaller market in Iowa that's probably a bit closer to what you are doing. 

I prefer the Redfin app for more accurate info and better search capabilities than Zillow, but it’s not available in all areas.

If you were capable of sourcing a house in a good market, rehabbing it, filling it, and managing it, you would make more money on the property than you would if you just bought it from Memphis Invest. 

I'm looking for someone with handyman level skills who wants to do more and is capable of doing more including some GC and project management type work.