What I'm hoping to find: I'm hoping to make connections, for mutual benefit; this could be investor friendly agents who have experience with identifying promising house hacks, investors who are looking for an additional financial partner, investors who are looking for a partner to help manage the load of projects (I am naturally drawn to planning and execution), and more broadly anyone who is willing to share experience and create new connections!

They may take 2.5 hours instead of 2 hours for a complete load but there’s no need to switch.

During this renovation period would you, as the lender, want an Actual Cash Value or Replacement Cost policy in place?

We have done lots of research about the city, but I know there are things that can come up from people with experience, especially since we are OOS (and out of country too actually!).

You can end this by showing them an actual utility bill.

Minimal changes to effect common entrances, no major shifts in load bearing, easy plumbing changes for wherever the new kitchen would be... it's a lot of boxes to check. 

Trying to get a split level (not a lot of sqft) on the market in the next three weeks and trying to decide on whether to open the wall between the dining and living room for a feel of openness or leave it as I have heard from two interior designers that the open concept is on the way out as we are more at home and liking our separate areas in the home.Pragmatically speaking the opening of the wall will be mostly a time drain with it being a load bearing wall and having to support the ceiling while rebuilding and all the drywalling necessary.

Quote from @Gregory Wilson: A few things there, Brendan.First, an LLC with you as a member and your (wife, son, pal, etc.) partner as a 1% member will file a Form 1065 which is about one tenth as likely to be audited by the IRS as a Form 1040 with a Schedule E rental activity (which I presume you will attempt to show is an active business).Second, you want an LLC because when your local Alabama handyman drives his girlfriend's uninsured truck into a van load of U of A medical school interns on I-22 when he goes  to get some shingles for your roof, on your business, you don't lose everything you have or ever will have to an uninsured claim. 

@Diego L.That's actually an interesting situation and a case where revocable trust may make sense.

You could buy 5+ cash-flowing houses and let a professional PM handle the load.