That being said, it's not true that multi-family will be as easy to buy as you age.

Not a perfect plan but it's flexible without age min of 59.5 to access or RMDs when you're 70 or whatever.

Anyway, thanks for the note  I hear you on reducing stress, not sure of your age, but I won't 'go there' on the stress and quality of life side of things....I'm more patient than I used to be for sure.As far as what could be next - sounds incredibly non sensical and irresponsible - yet, move it all including yourself to a Colorado ski town.

There are many buildings with systems reaching the end of their life - Galvanized hot water risers, leaking vent stacks, aging window systems, outdated elevator and fire safety equipment.

Here the agenda behind the prohibitive zoning is anti-gentrification which is merely going to result in disinvestment because developers are restricted on design and density and will simply invest elsewhere. https://codelibrary.amlegal.com/codes/philadelphia/latest/ph...

As you've noticed, rental property insurance is extremely tough to find in Louisiana right now, and will be highly dependent on the age of the roofs on your properties.

You'll be the lying anti-Christ and they, Angels

It's usually not the actual municipality creating issues except for that one that I think was near Clearwater/Tampa where they codified in zoning something anti-STR. 

Myself and family truly loved the property and house; just want others opinions on if this may be a mistake to proceed, or does this appear common practice for the age and location (upstate New York). 

@Charlie Brown, I'm not super familiar with your market specifically but I think this strategy works anywhere:- Find a boutique, niche, ideally aging broker/brokerage in your market, and start adding value.