I think both will go up in value over time and you will see a return if you plan on this being a home you live in for 10+ years.

Would it be possible for me and him to buy a new primary residence for him to live in, while we rent the house he is currently in.

We could be wrong, but it doesn't seem likely.Carini did the math for you early, if after repairs it assess for 240k as you suggest, you'll be able to refinance and pull out 187k, of which about 116k will go to paying off your previous mortgage leaving you with 71k to go plan your next move.This is very compatible with living in the house and getting roommates. 

It's cheap, it's near where we live, it needs to be rehabbed, it's the worst house on the block with a ton of potential.

I'd love to hear from any real estate investors who live half the year abroad (Europe - especially France) and half the year in the USA (sunny California, in my case). 

I live in SWFL and work in the commercial insurance field as an agent/advisor.

I live on the beach in FL and do deals all the time in Cleveland, I’d love any tips you’re willing to share!   

I think urban versus beach for example have different demographics.Not sure of your room dimensions but if possible I would do:Master: King + Convertible sofaBR2: Queen + BunkBR3: Queen + BunkBR4: KingWould also have pullout in living room. 

My wife and I love skiing but we live in TN so have to look out of state.

Can you actually live in the Miami metro area and avoid floods and hurricane damage?