Subscribed. We're going to look for something along the coast some time in the next five years. Similar strategy, @GlenFromTheMailRoom. Hoping to use it a dozen times a year, have it break even, be able to let friends / family use it, and build some equity.
We also have a strategy in place at our primary residence. We purchased seven acres, built a 1900 SF / 4-BR / 3.5 BA lodge at the front of the property, moved into it in early June, and will move into the main house at the back of the property early next year. Once we're settled, we'll start renting the lodge. We're right across from a big wedding venue with limited lodging available in the area, so I'm optimistic it'll generate some nice income.
For those of you with STR on the same property as your homestead, how are you handling property taxes, etc? I think I have a pretty good grasp on the management side, but I'm struggling with the financial / tax and risk side. I'd love some high level input from someone with experience to help figure out:
-Setting up a separate entity to "own" the property
-How to minimize tax implications, leverage homestead, etc
-How to reduce risk through the proper insurance policies