(important caveat: note i didn't say 'passive,' since it's not always passive no matter what you do. 

That really matters to me when doing business with someone. 

In my opinion, no matter what your margins are.

For your long term success it does not matter as much if you have 10 doors or 100, as if your portfolio value is 500k or 5 million. 

No need to pay me or anyone else for that matter to do it right.

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?

Consider options such as adding to down payments, reserves, or investing in other income-producing assets aligned with your financial goals.Next StepsTalk to Lenders: Discuss your financing options with lenders, including the possibility of a cash-out refinance or HELOC on your CT property, and explore the 10% down payment product for your next purchase.Real Estate Market Research: Identify potential markets or properties that fit your investment criteria, whether for house hacking in Las Vegas or remote ownership.Consult Professionals: Engage with a real estate agent, tax advisor, and possibly a financial planner to ensure your investment strategy aligns with your long-term goals and financial health.By leveraging your existing equity, navigating financing options, and resolving tax matters, you can position yourself and your girlfriend to successfully expand your real estate portfolio this year. 

With real estate, some of the biggest pluses aren't seen in ROE (or ROI for that matter, at least until you sell), namely appreciation, principal paydown and depreciation as a tax write off.

My focus is small to mid sized apartment syndications if that matters.  

I’m an out of state landlord so can not physically go to the USPS office.Thank you for your guidance on this matter…P.S. the USPS owns my mailbox