Please be gentle; I'm new at this and it's pretty complex :)Structure / Legal Details- we'd establish market value through a combination of comps from local real estate agent and an appraisal- attorney would establish all required "arms length" aspects including a mortgage at a minimum standard federal rate- LLC would pay us back based on a standard promissory note over 30 yrs Pros of selling to the LLC (I think)- A sale now would be the only time we'd be able to take advantage of the cap gains exclusion on this house bc we won't qualify for the "live there 3 of 5 years" rule due to the timing of our lease and our last time of residence. 

Our first two projects were conservative by choice and combined yielded in excess of mid six figure return. 

I like Bhargav's suggestion, maybe using a combination of leverage and cash if you have $1 million. 

His & my verbal conditions were he move in and we'd take care of bills combined while I took care of the mortgage for the year, then I'd refinance.

You might also be a good candidate for a small boutique hotel, an operator looking to retire will often entertain seller financing on fair terms and you could likely qualify for a SBA loan to help with your vision. 

DSCR portfolio loan that can combine SFH’s within a city and some potential rural SFH’s.

And also know that if you make more than $200-250,000 in combined investment income in a year there is a 3.8% Medicare surcharge on top of that 22% or whatever percentage.Best advice - start with a very cosmetic flip.  

This combined with the city's approval on a massive amount of construction spiked inventory, then crime went up, and then the rates went up.

You do not want to entertain short term renters.

When people exchange that 25-30% of income for housing expense to 40-50%, and combine that with stagnant income and increased housing costs for down payment, they'll never be able to save enough for down payment and closing costs.