I am looking at short to mid term rentals 

Consider Angie Medina with Orlando Short Term Rentals.

You will likely need to sit on the unit for a long time or reduce initial rent below the market for that unit to rent during the Winter. account for this by either offering a Winter special that will increase to market in the Spring or doing a short lease that ends in the Summer.

Shortly after, my strategist flagged that RTR was severing its ties with their PM partners in Harvest and would be seeking a new go-to team.

The key is to understand the capital stack, who is in line in front of you and what are their terms.The people who are getting burned may have known there was debt in front of them, but did they know it was short term or variable - did they know all the details to make a good judgment on the investment.If a property had 20 year fixed debt at 70% would you take that over 3 year debt on a variable rate at 50%? 

Find a realtor that knows the transitioning areas, there are a lot of "not-so-nice" areas in South Bend that would not work for short term rentals, but there are also plenty of great neighborhoods.

To keep it short and sweet, depending on your deal you should have plenty of options. 

Renting to people that aren't friends can be great, but also, one tenant can make everyone's lives miserable, so that's why I start with short leases in the beginning. 

Leveraging equity to purchase a short-term rental (STR) in Tampa Bay can diversify your portfolio and potentially generate strong cash flow, but it also increases your financial risk.

I recommend putting in your description there that your high-season months are for short term rentals and book at much higher prices per night.