You can deduct 25k of rental loss if you actively participate.

For FHA, here are the stipulations for military out of HUD 4000.1: "(7) Military Personnel Eligibility (a) Standard Borrowers who are military personnel, who cannot physically reside in a Property because they are on Active Duty, are still considered owner occupants and are eligible for maximum financing if a Family Member of the Borrower will occupy the subject Property as their Principal Residence, or the Borrower intends to occupy the subject Property upon discharge from military service.

It's difficult here to differentiate between giving good advice and advocating mentorship programs, workshops or courses to advance your one on one activity and thus speed up the learning curve and timeline to reaching and stretching your goals.I personally have gone the journey from DIY wholesaling, flipping, seller-financing SFR and international Short Term Vacation Rental management and then arrived at commercial multifamily and self-storage real estate syndication due to the fact that it offers the maximum scalability, economy of numbers and at some point truly leads to passive, residual income and thus to time freedom and choice.Send me a colleague request to kick the tires, set up a call and get a few burning questions answered in real time, one on one. 

Gotta bill some hours & get some work done before coming back here to play.

You may even want to set up different entities for the different type of activities you'll be involved in to maximize tax benefits.

However, would it be much more lucrative to do STR with dynamic pricing based on Bay Area events and UC Berkeley activities?

There may be other factors at play here two, but that was the most obvious one I could see on the spreadsheet you shared.

The only thing you need to wield is a legendary work ethic and to not give up.Man I’m 19, just dropped out of school, have been doing this actively for a couple months and am going to be a millionaire by my 20th birthday next June.

That should play in my favor. 

Account Closed I'm pretty active in the Nashville area and I run a turnkey ship down here.I can find deals, develop the property, renovate the property, put management in place, etcI will shoot you a direct message so we can connect.