That is where cash-flow shines as you have an income to use those tax benefits with.4.

I plan to leave them enough that they can afford to buy a house or start a nest egg, but I am not leaving large sums to them.

This phrase "Are You Leaving Money On The Table" could mean that you may have missed out on money in a deal that was there for the asking.

I think it's ridiculous to pay a tenant to leave, but it makes sense in places like California.

No I wouldn’t pay it and I would plan that potentially if I don’t pay it, they leave.

I had tenants that stopped paying rent for 2 years in NY during the pandemic and we couldn't kick them out, i've had tenants move out and leave someone squatting and NY made it impossible to evict them so I had to pay them off, i've had tenants destroy their apartments before they moved out (maggots in the fridge, flushing their kids toys down the toilet etc) so i've dealt with real difficulty.

As far as advising your parents to leverage the equity in the properties to acquire more deals, I would leave that to a professional familiar with the local market conditions and residential investment experience.

Issues with multiple national carriers leaving the state completely due to state regulations, massive loss ratios, huge increases in replacement cost values/limits due to inflation, etc. 

And the NNN leaves you only managing a long term lease rather than managing a property.And given your expertise, there's nothing wrong with a transition from farmer to landlord of the farmer. 

NY is a very tenant friendly state, so if he doesn't leave and she's on a month to month.