Personal readiness includes long-term plans, maturity, and market conditions.

As long as he is in this situation he can’t possible get to that point again.But, I may have missed something. ;-)

The construction financing is dependent on already owning the lots, so this funding to purchase the lots is the last hurdle.This builder grew up in the business and built homes in Kansas City for 30 years.

Places like Maplewood, Richmond Heights, Affton, etc. would be where I would start (if looking at long term rentals).

I used expeditors for specific projects in NYC, but in Long Island, I hired an architect who's also an expeditor, where I bough a SFH, the previous owner done unpermitted work.

Long term rentals are tough but maybe you could try looking into STR.

We actually rented the unit back to the existing tenants for as long as they wanted to stay because we didn’t have to do anything to the unit to start generating income.  

I would say it depends on if the property is a pain and what your long term goals are.

If it breaks when someone is in there, what is the rental income you would lose and how long would it take?

The repair costs will take multiple years to recoup and with the age of the property I'm concerned if it's even worth holding long term or get out while I can before I fall into a money pit and get stuck.