STR's are indeed a moving target in most coastal areas.

Do I kick them out legally and pursue the 15K or do I just kick them out and move on and not worry about the money. 

The person subleasing usually is a person that would not be able to qualify for the unit through the normal process.

I was working with an insurance agent from State Farm and they told me their underwriting process will take 3-5 weeks when we are already 2 weeks into the 30 day contract, so now I am without an insurance provider.

It will likely cost you more than 10% if you try to replicate this process.

Scenario: If one is to buy a new home to use as a primary residence ( till say Jan 1 2025), fix it up and get it ready for STR use starting Jan 2025 while STRing the initial primary until Jan 1, 2025, then move back to the initial primary and fulltime STR the new property..

Do you still live in it or plan to move out?

While you couldn't have used it for damages because you didn't know the move in condition, it would have covered the rent.

Hi Valerie, I moved to Columbus a few years ago (from Portland, Oregon which was super expensive) to become a full time real estate investor, and ever since, I've completed quite a lot of BRRRRs, flips, and own a successful rental portfolio here in Columbus Ohio.

My thought process: - Pros: Probably can get it for a discount.