The STR activity should typically be covered under an homeowners policy (HO-3).source: I was an insurance agent before I started my career in property tax reduction.

Hopefully you are taking your earnings to greener pastures.  

I'm ok with that part, but I am currently working a W2 and I am looking for a side hustle to earn extra money to buy my first property.

In other words, you earn the money one month at a time.

I took the first step to get to this point in my aviation career at the age of 15.

Do it under an LLC, trade in your car and depreciate the new one to cover some of the earnings.

You still have to make us earn the right for you to trust us.  

Typically, if you are earning a commission, you need to run it through your brokerage.

My goal is to secure my first Wholesale deal in the next 60 days, then another within 30-45 days, use the earned fees to purchase a duplex then cash out refi the duplex to purchase a 3-4 unit.

Because my orders are going to be TCS (as opposed to PCS), which is different then how the active duty does it, I have all these questions and want to avoid any serious pitfalls (or going to jail ;-) ).Going to jail is a pretty bad career move.