It current fetches about $55K a year in rents.  

Lots of us on BP have been doing it for our clients for years! 

I live in the house for one year either for free or with reduced living expenses.

I’m 21 and I’ve had this house a few years and lived in it for a period of time.

I just sold my business and in looking for ways to offset capital gains taxes stumbled across a strategy in which a STR can write off all depreciation in year one via a cost segregation analysis, thereby reducing taxable income greatly for a specific year.

I have a brand new house with a year of builder warranty, and so full property management might be overkill at this point.

Old roofs, old boilers, driveways, huge cap ex expenses that need to get taken care of.Read the Psychology of Money by Morgan House.

When using the Fannie/Freddie/Federal Home Loan Bank second home occupancy loan and you transfer title within the first year to an LLC that the borrower is majority owner of it will not trigger the due on sale clause as long as you can attest that it will continue to be a second home.  

I'm a big fan of the Yukon Solo Stove with stainless steel lid, which turns into a legit coffee table when not being used for fire - it isn't the cheapest set-up in the world, but the one I put into one of my LTR properties 3 years ago still looks nearly brand new, and was a huge selling point when I was getting it leased out.  

There would be a 3+ year minimum hold and the opportunity to sell later, if desired.