I had one unit deliberately flush an entire box of unused feminine hygiene products down the toilet in order to clog the sewer line.  

I am currently in dental school in Cleveland with the goal of getting my first deal this summer while on break.

Again, STR are not technically allowed for "tourist homes" in very many places in the city as most, but not all, R2B zoned areas are limited in the number of residential houses in them, but are many times commercial spaces such as small dental offices.  

Chickens make nice eggs but they aren't known for hygiene. 

Face masks, proper distancing, proper hygiene/hand washing.

We rent an AirBNB on the beach from a gentleman who used to own his own successful dental practice, and now he does AirBNB full time. 

How much cashflow do you need to create this security to get out of the dental rat race?

If you have a career that's less affected by the economy (health, dental, vet, etc.) and are cash flow positive thousands each month, then you can afford gambling on an appreciation asset.

I want to make this area work for me because I have a good shot at the dental school there.

I'm a dental student in Birmingham, and have lived in Birmingham for 2 years and near Birmingham my whole life.