There is a lot of uncertainty in the market for institutional capital, which funds a lot of these types of loans. 

There is of course the agents, the brokers, the mortgage and lending side, the title companies but also the whole construction side would be part of real estate.

You'll want to know the answer to these questions or you can get into a tough situation, especially if you are using commercial lending with DSCR requirements and covenants that you have to perform to.

Knowing my end goal is to move to another state (Sperryville or Staunton, VA) and 3-4ish hours away to start a small hobby farm, does it make sense to pay off these properties rapidly in the next 5-6 years so that I have a total clean slate from a lending perspective in order to finance the land, house, and buildings, or does it not matter?

I have no idea whether these are or are not allowed in OH as I don't lend there, but a loan with a 2 or 3 year prepayment penalty would likely have lower points and fees because you are basically paying that penalty up front as a fee in this loan.

I'm constrained to being on title so completely understand that I'm accountable to the lending debt - not concerned about that.  

I did a investment lending to a company for land development project.

Ultimately would like to make connections so thank you SO much for your time and willingness to lend a hand to a new investor who is staring down into that water, wondering if this is the right leap...Much appreciated,Jon

I am not a W2 employee so constantly limited by my DTI when it comes to bank lending even though I am savvy with saving, house hacking, etc to keep my cost of living down.

There is a home in Tampa I went UC with a wholesaler and told him I was closing it conventionally which they were fine with.Long story short the home is a triplex and zoned as a SFH so the lender will not lend on the property forcing me not to close and the wholesaler took my EM.