The first thing I want to point out is that it may be wise, in your thinking, to separate the property itself from the STR business that's being run from the property.In the old days (as recent as 10 years ago), people buy a vacation home to enjoy, and they leave it empty when not in use. 

Quote from @Jonathan Weinberger: Hey BP community, Every so often I enjoy writing about my investing experience here.

We'd love to escape the cold Dutch winters and enjoy a warmer climate.When we're not using the property, we plan to rent it out as an Airbnb to generate passive income.

My wife and I are tied to this area due to being in proximity to family and we currently enjoy a farming/hobby farm lifestyle that is a big part of our family culture.

I haven't sold yet, I've been analyzing property to get a head start on the 45-day timeline of identifying the potential replacement property (and because I enjoy analyzing property). 

Since relocating here, I've enjoyed expanding our own portfolio while also offering services to OOS investors looking to invest in Indiana.

If I pay it off, I could maximize cash flow earlier, reducing financial stress and allowing me to focus on other ventures or simply enjoy life more.On the other hand, I know some people advocate for keeping cheap debt and using the extra cash to invest elsewhere for potentially higher returns.Why I’m leaning toward paying it off:Security: No debt = peace of mind.Financial freedom earlier: A fully paid-off rental would give me a significant monthly cash flow?

@Melanie AlzugrayInvesting in a resort you and your family enjoy is a fantastic approach.

Quote from @Patricia Steiner: @Owen RosenNo...here's why it is 'additionally insured:"  "An additional insured is anyone who enjoys the benefits of the insurance policy that is not the primary policyholder.

I'm a local real estate broker, investor, and manager (100+ rentals, mostly Airbnb/STR and multifamily).House hacking is a tried-and-true method and in Sacramento you can produce some meaningful income while enjoying the appreciation and tax benefits of owning real estate.