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.

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

If you do a case study also consider what market appreciation and mortgage paydown would occur in both scenarios.

How ‘hot’ is the market?

There has been some hesitation for me to sell due to the fact the rental market here is averaging $2,500 in rent for my area and property, I make great money now and have funds to cover vacancy and repairs on the home, but I would like to be able to afford a nice rental for my fiance and I to live in while we save for our primary residence.Shoild I sell and take my profits (60-70k net) and throw into an investment closer to where I will be living or should I rent, cash flow and build equity in the property. 

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

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.

If not I would be paying market prices.

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)? 

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.