@Angel De La Mora Ovies Hello.Being honest your questions sound more or personal choices that you might want to ask yourself deeper on.

If you do choose the REI route, if a crash happens have your son take a couple roommates for $400/month, Air BNB it for the summers when school is out, put up solar panels, figure something out. 

I have one I was looking at on Long Island NY and another one in Delaware. 

The DST (Delaware Statutory Trust) is not obligated to pay the $800 franchise tax mentioned above, and can contain as many assets as you like.

My neighbor just put a bunch of solar panels on his house even!

Just as you said, as for where we want to be long term, after his two years we will likely end up selling the NY property in an effort to consolidate our portfolio closer to where we want to be long term in the Delaware area.What I wonder is it a good idea to try to live in flip with a low potential profit margin or buy and hold in a potential risky area to live for basically free?

If you still want to be able to drive to the property within a few hours, I would recommend checking out communities in Pennsylvania or Delaware.

I also think you can de-prioritize your dependable relationships, as you can't really know if those relationships are dependable until you start using them.

Looking for General Contractor in Bear, Middletown, New Castle, Wilmington are in Delaware state.Please let me know if you know or have a good company to work with.Thank you  

Where I am from (Delaware) a 3 bed 2 bath can rent for 850 a month.