Uncle can sell one as is, take the proceeds and fix the other one up, and take the $250k capital gains credit on top of the reduced long tern capital gains.He dies, kids get the stepped-up basis.He could also look into a 1031 exchange, but at his age, that's a lot of work.Your off the cuff remark raised a host of issues, and tells me that you're not giving us the full monty when it comes to relevant facts. 

You're correct no real estate taxes, but you can and do get taxed as business personal property.

This is a very common issue with aged persons striving to stay in a residence not capable to fit end of life aged needs.

Quote from @Jason Anderson: "I'm late to the real estate game at my age."

@Mansi Ranafind local, in person meetups and go to thosegood luck

I am under 18 years of age and I am trying to set myself up for success after schooling.

In this day and age, the physical location of a real estate brokerage shouldn't matter.

I did have long term tenants like this and sent them a whole list of VA and age related help which they never applied for so you can point them toward community resources but people will do what they will do.

My personally....I like Woodlawn more than Pilsen @Anne Connor! 

For investors using DSCR loans, I’m curious about your preferred minimum DSCR.
Do you stick to 1.1, 1.2, etc.?
What ratio gives you peace of mind in today’s rental market?