If you were in my shoes, what would be the best course of action you would take in order to attain your first property, get the rental income generating so I can eventually with time generate more properties and with more properties, more cash flowing in.

Whoever doesn't pay their dues or assessments, the HOA places a lien on the property and could eventual foreclose on your property to get their money.  

I'll definitely get all of my investment and money spent on overhead back in the refi, but do I continue forward with the BRRRR, take the small loss each month, and bank on rates eventually coming down some more where I would refi again to bring the payment down OR pivot to flipping it where I'd make, easily, $40-50k net profit AFTER setting aside capital gain taxes?

It would be more money to setup and more stress to manage but likely get you above market rent and enough to eventually cover the mortgage for a while.

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.