One advantage of living there.As long as you have a real estate attorney willing to work with you (as in YOUR attorney, not the banks) you don't need the broker, though of course there are disadvantage to not having a good one.If you have the downpayment thats your best bet, line up your financing.

So then I started thinking about entering some long-term leases in STR vacation destinations, as long as I can cash flow above my monthly rent payments, right?

As long as you aren't thinking that you are going to buy a 2-4 unit property every year and build a portfolio of cash flowing houses in 3 years to support you, then you will be happy.

Since I own the land, I can get an homeowner exemption meaning that I do not have to be a licensed GC and I can do everything myself as long as I will be present for all the counties inspections.

Much less risk vs stocks in my opinion as long as you do your due diligence.

As long as you have the appropriate documents/agreement between yourself and the mail-person (once they find you a deal), you should be fine.

If you like or dislike the 4% rule is fine as long as your thinking about your Financial goal.

I'd stay there for as long as possible and use the equity in your triplex (HELOC/refi) to buy more investment properties/house hack.

-Matthew Olszak's math of the situation how even if you lower the rent you'll still make up for it so long as you don't have a month's vacancy.

But if you were a licensed builder you could do more as long as you did work on them.