I'll give an example of what I am thinking of doing and if this is a viable strategy.

Full disclosure I am relatively new and learning and taking my lumps as I take action as well as I speak with more and more people.

I've mentioned this in a few other posts, but I am sort of stuck on Long Island for another 4 years or so.  Then I am certainly moving out of state.  I pay outlandish rent, like $3k a month. I want to at least cut this in half.  By the fall I will have disposable income. Probably about 90k worth.  In lieu of house hacking, or any other strategy is the below doable?

I have an acquaintance who bought a home in Florida (by the water) and sort of AirBnb's it throughout the year blocking off times she wants to live there while still "living" in NY until she can permanently move.  According to her...by renting in a desired area for weeks at a time she is able to cover all her expenses in only a few months and allows her to support lots of her living expenses in her current property in NY.

I am well aware, that there are variables such as how much she bought the new property for, how much she put down, how much rent is she getting, where she currently lives now, etc.  But is this a strategy of sorts?  Is it sort of a buy and hold with the intention of living there at some point while covering all costs of the property and then some.(And no, it doesn't have to be Florida, I am still weighing my options on where).

Anyone do something like this?  Or have clients or associates who have done this?

My parents do this with a condo in Hawaii. They bought it fairly cheap, did a full remodel and now have it on airbnb. They usually go 2-3 times a year and stay for 2ish weeks at a time. As they get closer to retirement they plan to increase the lengths of their stays until they are fully 50/50 residents. When they are not there, it is an airbnb. It's income producing and they are able to write off travel expenses when they go to visit. There are definitely risks associated with this method because your income can fluctuate drastically, especially in the beginning while you are still working on building up your reviews (or in the case of a global pandemic). I would say it can work out well as long as you can afford to pay the mortgage/expenses if it is not occupied. But I wouldn't get into without a really stable safety net.