I only want to focus on buy and hold investing in long-term rentals, specifically SFH and MFH.

It sounds like you want to let the person live there for as long as they are alive and then the house converts to you.

One is an MTR where we rent long term for 6-7 months then becomes an STR for the summer - the ring camera stays and so far no one has asked anything about it.LTR may be a bit different.  

In terms of giving away equity; I am not sure if this is too far down the road, but getting long term debt on the property is a consideration as an exit.

alot of Insurance company stop writing policy in long island NY. 

For Investors By Investors (FIBI) has a Long Beach chapter. 

As long as you're OK with that, you can proceed accordingly.

My family owns a 2 BR 1 BA in the area and I have looking at using this property as a STR, as long as the house is zoned for it.

How long has the property been there and has it ever flooded?

I’d consider keeping it at a rental long-term or may need to sell it.