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It just doesn't strike me as that odd or out of pocket that an older, single mother of a disabled son can't afford 1500$ in rent.

Learning about dynamic pricing is a great next step to boost your revenue by adjusting rates based on demand and seasonality.

We‘ve also been considering the idea of going to short term during the summer season and keeping mid term sept - may.

Here’s to hoping the rest of this hurricane season is uneventful.  

It is true that certain policies will accumulate significant cash value, but you either have to put in several thousands for a certain amount of years and let it season for a bit (Life Insurance Retirement Plan) or you pay your monthly/annual premium for quite a while and wait until you're in your 60's or 70's+ to have access to a good amount of cash value (Variable Universal Life).

Since I'm approaching the stage where I'm looking around for a builder what are your thoughts on working with a seasoned rehabber that wants to get into GCing new construction?  

Ohio and Pennsylvania have lots of older small multifamily that I do think is very suitable to house hack - sometimes you can buy a place with a studio or 1 BR that also has a 3 BR or a 4 BR, you live in the smaller unit and you rent out the larger unit. 

Is that income seasonal or long-term stable?

I manage a few properties in coastal NJ and the season is 3-4 months.