Contractors are hard to come by at the moment and all prices are elevated. 

In WA, at such elevated prices, if you decide to take a mortgage and have a property manager it would be difficult for most locations to cashflow positive.

Is there any smokeless cigarette smell nastier than when a smoker comes in from a smoke break and gets in the elevator you are already on?

Best scenario in my opinion with the least headaches could be to sell that home and move the equity into a 400K home that is paid for in full, this will elevate a lot of stress and give him time to retool and overcome the rotten economy forced upon us. 

In California all multi unit buildings with elevators need all units to be adaptable.

Ah, the elevator pitch! 

For finding places with low HOA look at low rise buildings (no elevators) and 2 story townhouses that aren't new construction like townhouses built in the 90's or early 2000's. 

You determine similar numbers for each major element ...roof, exterior paint, windows and doors, water supply and waste systems, elevators, etc.

75% of the time they say, "Yes", and I proceed to give them my elevator speech about what I do and how I can help them move properties. 

So with current economic conditions (rates are elevated and going higher) you may need to wait for 1-3 years to catch rates at a better point.