Eventually he helped me broker an owner finance deal with the previous owner.

Eventually I hope to get to a point where the extra rental cashflow will suffice for savings and I won't have to take out anymore 401k loans.Keep on crushing it Brad!

Don't give into impatience, or others telling you "just do it", or "the property will eventually cash flow or appreciate".

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.