Not a fan of some of those locations. 

So, by avoiding frequent turn over we are making our money back that way, but there is no way you can justify the cost through a rent increase.

I'm not a big fan of "estimating" just about anything.

I just need something to help drop the temp in the late summer months in conjunction with strong ceiling fans.

In that area people would frequently convert houses into several distinct apartments and rent them out separately.

I see where you are going @Steve Morris, and I am not a fan of those types of wholesalers as well.

I frequently come across these smaller lots that would seem to be perfect small multi developments (duplex-quads) and i don't know enough about them to know if i have a deal.

When you have 10s or 100s of millions of dollars that you need to get a return on your options are more limited than if you're an average investor trying to create $10,000/month in passive income (to throw out an arbitrary number that I hear used frequently). 

(Die hard Disney fans will still show up, and they will happily wear a mask and do whatever it takes.) 

https://www.bizjournals.com/louisville/news/2020/08/12/2020-kentucky-derby-downsizing.html
This was to be expected. Honestly, should be a relief to airbnb owners that we are having a derby at all!