(after pay off, and cover insurance and taxes, profit of $1100 per month).Problems: We initially were trying to get properties paid off in 15 years or less so we would have profits every month in a short period of time.

Hey Lucas, I've been investing in Detroit since 2019 and currently hold 12-doors there.I've done it all... buying with tenants, Section 8, full gut rehabs (to the studs), cosmetic BRRRR's, and I even run an STR there.I live in California currently but lived in Troy from 2017-2022.

You can usually also benefit more by simply using the seller or builder credit to do a simple "Rate buydown".The first rate on the buydown is a "teaser" rate that only last for a short time 1 year for example but a true rate buy down is for the entire term. 

Is short/mid trem rental arbitrage profitable?

All the properties will be on Section 8 (longer term tenants).

I started a post yesterday regarding VRBO Terms of Service.  

I finally got around to reading the new terms of service.  

That is what we use.Remember it is a Short Term Rental, not an AirBNB.

How do you analyze a property for a medium term rental?

I would be inclined to work with them on this as long as it was a short visit.