But when it comes to watching people say we are headed for a market crash like what happened in 2008, this frustrates me.

Even if they’re butt heads.  

And I think you have a good amount of control whats happening in your own head, even if you are in an unhappy industry.

Everyone hit the nail on the head with their responses.

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 don't have a rapid dialer, but my understanding is that they upload this list to speed dialer.

Some people do extremely well with section 8 but if you are diving head first into it, you may want to start with a traditional rental first to get a feel for it. 

@Mark Pruitt We almost exclusively use River Ridge Escrow in Cedar Rapids, closer Melissa.

Compound that with a squirrelly seller and tenant, and you’re not just seeing red flags, you’re being beaten about the head and shoulders with them. 

Rhode Island requires proper notice for rent increases—usually 30 days, but considering the circumstances, giving them a heads-up now would help them plan and avoid surprises.