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.

If not I would be paying market prices.

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.

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. 

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)? 

Let me know if you are interested in out-of-state investing in the Memphis, TN market!

Every market is different, but for the long term assumptions.

You paid the market price and own the liability.

Then also decide whether you want to chase down loans to find and originate or buy loans on secondary market from others.