I have 3 years left in my military contract but would like to start out (even if it is slow). 

Alaska will always hold a special spot in my heart.

I would get it under contract and use your inspection period to figure out the rest. 

Well, I don't know how many deals you guys are getting, but after 5 months, several hundred underwritten deals, and several best and finals, we finally are under contract on a 98 unit value add.What it took:- $100,000 EMD- No Finance Contingency- $50,000 Good Faith to lender- $15,000 to attorneys for the PPMBig shout-out to my partner, @Sam Grooms.Now we just need to close...

I just put my first deal under contract and like you am doing an owner occupied or househack for my first deal! 

I understand that you can include the assignment fee in the principle price in a contract but when can a profitable buy high assignment fee be a problem for a seller or end buyer?

I called around to a few property managers to get a lay of the land while screening them and have a property under contract.

They're under a two year contract and so far they've been there one year.

Question is, I'm on good terms with the renters, is there a way to sell this on more of a handshake/privately recorded contract that would work out? 

And then after you pass you will find that everything you learned so far provides you will a good base and background but very little of the actual practice of real estate like MLS, Contracts, negotiations and procedures; you'll need a good broker/mentor for that.