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’s highly passive and there not much to do other than network and marketing.

I'm eager to learn from your experiences—what strategies or processes do you use to determine expense figures in your market?

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.

Make sure that the market there makes sense for your goals to invest.

As a long-time high-level Rentlinx.com user, the journey since Rentlinx.com removed its marketing offering roll it into AppFolio has been an absolute nightmare!

The market is tough here.

In this part of the market cycle, newer vintage assets, median incomes of at least 50k, washer dryer hook ups, more two beds than ones, townhome style assets.When the broker showed us the deal we didn't have to waste time analyzing it.

Yet, as I closely monitor the current housing market, I realize that stability and thorough due diligence are paramount before taking ownership.

They typically have below market interest rates and can be used for house hacking a 2-4 unit.