It seems like every city, county, and state has its own rules, permits, and tax requirements for short-term rentals, and I’m finding it overwhelming to navigate all the different layers of compliance.For example, some places require business licenses, transient occupancy tax permits, or even special zoning approvals.

It's tough out there to make numbers work!

I believe there may be special exemptions around a job relocation or other extenuating circumstances.

@Daniel BoucherThis is a tough question.

Right now, land (unless in a hot market) takes a special type of buyer/developer to turn it into money, so you're better off finding the thing the people with the money want. land tends to sit a long time...

My girlfriend and I are looking to get into Multifamily real estate investing and have also looked into the possibility of house hacking, although a good affordable property seems to be tough but not impossible in this area.

Keep in mind that this is also a very tough time to be entering the market as an agent because the inventory is so low.  

Building a relationship with local real estate attorneys or agents specializing in STRs in the area can save you headaches down the line. 

Cleveland is a great cash flow market but it's tough to navigate from afar.

@Sonja Revells , after reviewing the agreement you uploaded, I realized it could be a bit tough to fight for your EMD due to these sketchy clauses.