It takes getting off the road everyone else is driving (the MLS) and putting some work into it.

I offered to buy the property from the $28B foreign company which kept them from having to tear down the buildings to mitigate the vagrant problem and also from their obligation to pay the rail road for the long term lease.

Clearly, shes not happy and an unhappy tenant usually results in more issues down the road, and you can bet they'll be expensive issues. 

Split the $20 to buy yourself lunch and dinnerIf you are on the road, daily per-diem should cover a lot of your day to date living costs.If they send you on the road, you can potentially airbnb your house.Best of luck!

Beyond carefully vetting the tenants, how can an investor protect themselves from squatters if we want to sell years down the road?

I would think about tenant expectations and how much maintenance you’re willing to manage down the road.

It would be wise to rectify it before transfer of title so your starting off clean and hopefully won't have any issues when you go to sell down the road. 

Over the summer my wife and I bought our first condo with the idea of renting it out later on down the road and kicking off our investment journey.

But your main killers; road access, water access, fire hydrants, flood plain, storm sewers, Storm ponds, road surface requirements, etc. 

There are a lot more details that go into two VA loans and the downside but transitioning into a conventional loan on the  investment refinance will save you a lot of frustartion down the road.