Mapping out a potential unique opportunity - ideas welcome!

[Daniel Gugliotti]

I have a potentially unique, but low barrier entry opportunity in front of me, but I am struggling to put the pieces together in a way the make sense for all. 

I live in CT and I have relatives who would like to "snow bird" to Florida at some point soon. They have a house with an in-law apartment (essentially a 2-unit MFH) that needs some work. The house also happens to be right next door to a wedding hall. Seems ripe for the picking to BRRR the home. Ideally, I would STR it to either the wedding hall or seasonally, although the purpose of snow-birding is to be in CT in the summers (wedding season) and Florida for the winters. The less risky/more logical avenue seems to be to LTR one unit for more predictable cash flow and STR the other unit to create availability for my relatives when they come to visit. It's worth noting on the STR side, CT is not exactly the AirBnB capital of the world.

But my struggle is finding/pitching the value add to them? They would need cash to buy/rent seasonally in Florida, so is there a scenario where they sell the house to me, obtaining the cash they need to buy in Florida, and then rent one of the units back from me in the summers? Is that taking on too much risk? Will a bank see the same value that I do and be willing l do a DSCR loan based on LTR and STR on the same property?

Any ideas, feedback or suggestions are welcome! Fire away!

[William Collins]

Daniel, while Connecticut isn't the Airbnb capital of the world it is still a very viable place to do so. The question that comes in is the value of the houses and what town it is in. You'd be amazed that there are a lot of demands from just people who want to get out of the city or have work assignments that bring them to Connecticut. In this case, you might want to mix it up and be partially a mid-term and short-term rental. The best way to finance this would be to acquire this as your primary residence if at all possible. Especially with the in-law unit, you may be required by the town to occupy one of the two units, please look into your regulations.

The question I have is why would buy it at all? If your parents have a long-term mortgage on it already when offer to manage the property while they're in the Floridas for a split of profit?