This just might be my opinion but at this point even if you're out one months rent which definitely sucks it may just be easier to start showings.I don't know what the L/T laws are in your county/state but perhaps send a notice to the emergency contact with something to the effect of pay or quit with an option for a release out of the lease and be done with it. turn over this unit and get it out on the market again.

With the season in Sarasota County considered November - April, what is the best way to market the property as a Medium Term Rental (at least 30 days)? 

I've noticed in my area that houses that have been converted into 2 units tend to sit on the market for much longer and sell for much less than traditional single family houses with similar sqft and finishes.

I am also in the cincy market I will send you a connection request.

To succeed in hard money lending, know your local market well, value properties accurately, and carefully evaluate borrowers.

The last real estate investment I ever paid capital gains tax on!!!!!

I wanted to secure a property in Savannah, because of how much the market is growing.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

My partner and I are fresh into the real estate investment market and want to learn as much as possible.

Considering their LTV is at market or debatably below market (depending on the asset), if the interest rate or loan terms aren't advantageous, I'd also suggest getting quotes from other lenders.Since you are located in upstate NY, I'd look for local banks.