u/MLin502

We are experienced rental property owners, but that is long term rentals that we self manage. We are exploring the idea of purchasing a vacation rental property but we would need to pay someone to manage. I have no idea what the going rate for that is in the area and was wondering if anyone had any idea. I’d want someone local who takes good care of the property. We love Anna Maria and 30A so we’re really only considering those two areas.

We are experienced rental property owners, but that is long term rentals that we self manage. We are exploring the idea of purchasing a vacation rental property but we would need to pay someone to manage. I have no idea what the going rate for that is in the area and was wondering if anyone had any idea. I’d want someone local who takes good care of the property. We love Anna Maria and 30A so we’re really only considering those two areas.

We have owned rental properties for almost 20 years and have about three dozen units. We also have very good paying W2 jobs. We historically haven’t made a ton of cashflow on the rentals because once we bought larger properties a few years ago, they needed work so the profitable properties funded that work on the new property.

Now we’re starting to really cashflow with the properties and we really don’t want to, we don’t need the income right now (we want it in retirement) and it increases our tax burden significantly.

We’re thinking of a 1031 for a vacation rental property. Maybe put 40% down and we anticipate it would take a loss but that’s the point. A loss that is offset by the other properties, and we could even fork over some money if we need to. Ideally the property becomes a 2nd home for us one day, I’m aware of the rules around that.

Is there anything I’m not thinking about here? Or does this sound like a decent idea?

EDITED TO ADD we have always planned to have a retirement condo at the beach. This purchase would not be solely for tax reasons, but rather that we are rethinking how we get to that purchase of a vacation property.

We take really good care of our properties, we fix things instead of Band-Aid them. Rents are always a touch below market to try and not have things to empty. We self manage and fix things ourselves, so our expenses are just not as high.