Hi Landen!
First off, thank you for your service.
Secondly, you have come to the right place, and your growth mindset will take you far. You will be swimming in information so being intentional is the right approach. First, define your "why" and think about what you really LOVE to do, that you would do for free because you enjoy it so much. That will dictate what asset class you may want to consider, and WHO you will need to rely on for their expertise. Someone who gets burned out because they did not align their natural compulsions with the right activity will never be able to compete with someone who sustainably loves what they do and would do it for free. Be that guy. That said, here are some ideas based on your post:
- VA Loan + House hacking...Yes. 100% YES. David Greene says "You should be house hacking 1 house every year."
- Short term rentals: Read Avrey Carl's "Short term rentals, long term wealth" - it got me started, but I will caveat that "mature vacation rental market" does not equal "no regulatory volitility"...so be prepared to deal with that. local governments of resort destinations are still trying to figure out how to deal with the onslaught of AirBnB demand & backlash from locals. I own 2 STRs...so far. One in City Of Big Bear Lake, CA, and one in Big Bear City, CA. Similar city names, totally different regulatory departments.
- Long term: I am looking into self storage myself...no toilets, no tenants, and if they don't pay, I keep their stuff. : ) Sounds easier than it probably is, but enticing.
- Read "Buy, Rehab, Rent, Refinance, Repeat" by David Greene.
- Read "Finding and Funding Great Deals" by Anson Young.
All three books are on apple books (and probably whatever Android uses) if you are into audiobooks. Hope this helps!
Craig
