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 have looked into REI Nation, they market really well for new investors but I am sure they have big fee's and a few horror stories.

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

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.

With a better understanding of your budget, you can make more informed decisions to ensure you are putting the money towards things that will not only keep your properties running, but to also increase the value of your properties.Financial Plans for the Future: Having a cost segregation study performed and using it as a planning tool allows you to have a roadmap for the future including being able to strategically utilize other tax benefits alongside it.

If not I would be paying market prices.

It is still advisable to see what is on the local market and see what is selling as you develop your plan to renovate a property.