And most folks want to "roll in" this cost into the loan.

WTF, RU forces are not in any threat of rolling armor into D.C. but they sure as hell could roll it into Berlin. 

The regulatory push in some HOAs has been stalled due to the STR victories over The Hideout. 

The lender is pushing you to do this to get an FHA loan.

My realestate agent keeps pushing me to sell them individually, and I really want to keep my tenants with a landlord.

The $1,500/sq. ft. estimate seems reasonable since 4 Dewey Ln and 597 Beavertail Rd support that pricing.One thing to consider is whether any of the comps had unique features or lot premiums that could push their price per square foot higher than what your property might command.

And you have to constantly put work in - this system doesn't turn unless you keep pushing it. 

You'll need to roll it over to a custodian (a company that holds and administers the IRA).

I suppose I am wondering how to find interested real estate investors in the area or look for interested agents with input into what my best move would be really get the ball rolling

I pay a neighbor's kid $10 a week to roll 2 cans down to the street and back.