The reletting charge doesn’t release Tenant from continued liability for future or past-due rent; charges for cleaning, repairing, repainting, or dealing with unreturned keys; or other sums due.

I did a double check on my properties (I do this regularly anyway), my discounts remain as I had them previously (I do offer different discounts for length of stay).  

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?

Purchase price: $4,000 Cash invested: $15,000 Bought land with 5 mobile homes on it cleaned it up now it's my construction yard.I would like to buy the land behind me and convert it!

So you're the guy cleaning up the yard, trashing out the house, working the rehab or supervising the rehab, learn some of the work you could do without much time...paint, demo, basic repair, cleanup, etc.   

Your challenge is to make your request seem like it’s part of their regular, bureaucratic tasks. 

Similar with a SFH: I can at least get in the market with a 5% conventional loan not expecting cash flow but hoping appreciation will help me out in the next 2+ years and I will at least be able to put up the remainder of the expenses since I do live with my parents.I am young so I could be overthinking, but my end goal is to have a portfolio where I can cash flow enough within the next 5-15 years to let go of my job (5k clean a month).

.- Your experience with your properties which do or don't have acreage / views / streams / ponds- Your experience with access to good labor (cleaning & handyfolks)- Your experience with the renters.

You can see regularly companies and some individuals here on BP that like to play games and it happens to them.   

Unless the place in an amazing location that couldn't support a full size home, you are better off doing a regular place.A tiny home isn't considered real property.