Anticipating that the property will eventually go on the market, I'd give them an offer sheet with multiple options to sell to me in liue of just of subject to. 

Ideally I am looking to purchase a place as an owner occupied rental and rent by the room to those who I already know need a place to stay and eventually turn that property into a September-May student rental and rent it as a vacation home during the summer months!

anyhow, I'm more than happy to put in work and eventually replace my job with it if possible.

Definitely take advantage of having two W2 incomes right now to buy properties and be sure to each use your VA loans once or multiple times if it fits with your goals.Just know that if you are serious about building a real estate portfolio, you will eventually get to the point where you can separate from the Military if you choose and go full-time in real estate.

Karma will catchup to them eventually. 

People say to wait for the housing market to go back down because it will eventually.

After talking to numerous lenders, I eventually discovered one in Carlsbad CA that said he had a lady doing deals in Palmdale with the same numbers I was underwriting. 

He was a bit of a scatter brain, but always paid eventually.

If you aren’t at risk of losing right away, take a day to think over each counter-offer.If you take a day every time they ask for a concession, they will get frustrated with waiting and will eventually just give in to your requests.

Equity, New York will yield more equity and will eventually return additional funds for investment over time, but Vermont will be able to Cashflow sooner with the ability to increase equity through repair, but it may be several years before it reaches the value of the New York property if ever.