Details below:-This would be our primary residence, not an investment property (but it does have optionality via an ADU setup)-The seller is interested in selling and relocating out of state in 2 years when they retire-We have a primary home (that has been a cashflowing rental) in the same town.

The interest actually goes back to me so it’s essentially just an opportunity costs question about losing $50k of retirement investments with effectively 0% interest. 

The cash flow from the investment would be intended to replace a W2 income and the funds would come from my retirement account.

I've met his kids who are in there 40s and I've spoke with people where he banks at to confirm income since he is retired and they spoke highly of him.

He was a minority with a minority attorney pro bono (social justice lawyer) who thought they were going to retire on the $2,000,000 they would get me to settle for.

We are retiring in a couple of years to the Midwest to be closer to family.

I  know a few people who have retired from a few different airbnbs down here in West Palm Beach.

Hello all,I spoke with a mortgage broker today in regard to purchasing a home in FL for my retirement in approximately 9 months.

Similar green energy investments could be considered if you can make the numbers work (credits on some types of low income housing can be north of 50%).Depending on how long these properties have been held, they could consider implementing cost segregation studies via a change in accounting method to accelerate some depreciation.The operating proceeds could be re-deployed into new properties where cost segregation is an option to accelerate depreciation to offset proceeds.If the properties are low basis and we are not maximizing the 199A deduction, maybe considering an S-Corp structure for management to be able to participate in retirement plans and also generate wages to use as a 199A base. 

A married couple in their 70s that have previously owned homes for 40+ years and are now retired with no debt, no kids, and 50 years experiene as adults should not be looked at the same as a boyfriend/girlfriend in their early 20s that have never owned a home or rented together before, still paying student loans, living paycheck to paycheck, and financing that 2018 Dodge Charger in the driveway.