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.

Look at their marketing strategy.

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. 

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.

I did tell him she’s got till Friday or I’m filing complaints with all the agencies you all told me about.He told me he was going to tell her if she didn’t get this handled asap he was going to tell her he would no longer be her broker.  

Let’s say you own a land lot worth in the market only $20k, but because land prices are all over the board, you have a legit appraisal at $50k.  

Upwork also has some cold calling agencies you can hire as well on there and you can read reviews on them from past clients to help make your decision.