@Andrew Steffens hit it on the head, in my opinion.

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

While you may have a 2Br that is not for the "typical" sized family, you will have many people also looking to downsize from their larger homes that they are holding on until the summer to list. 

This ticket also comes with one of the workshops on Sunday.

I do a lot of business on the nearby barrier islands of Anna Maria and Longboat Key.

It's an FHA Streamline Refi, we've done it twice on our home.

In either case look to list/find on Furnished finder. 

I'm also working on ways to separate myself from the majority of these wholesalers that are independent and not offering the best deals.

Can anyone shed some light on this for me?

Do you lower prices, offer promotions, or focus on longer-term bookings?