maybe you can form your own mastermind / small group of local people in your same situation and work on strategies together.I think @Marcus Auerbach totally nailed it. 

While this is less tax efficient, it would be less work / less stress.

Build an SMB on top of your real estate (the reverse of #2)Short-term rentals and high owner-participation real estate businesses can have great returns.Obviously not for you if you just want passive RE.We are in the deep end here, where each case should be judged on its own facts and merits by your CPA.You should hire a professional to review your particular situation before you make an investment.

I was wrong.The situation regarding data in FL is, unfortunately, not the same as other states.

Stick with classic neutrals to appeal to the widest range of buyers.There are situations where clients touring homes immediately pass on properties due to strong or unusual color choices.

While it is rare, there are situations where a Broker is not a member of an MLS. 

Situations like this I would have done a WT before offering.

.- My Resources / Constraints: I'm in a by no means unique, but perhaps less common situation for those getting started; I'm a somewhat senior software engineer at a tech megacorp and should be able to save a couple of down payments per year for lower priced houses (100-200 in my area), or perhaps one medium priced house (300-500).

I appreciated Zach's call today and the time he spent listening to me, and also sharing what he could do to find a solution to my situation.

Quote from @Jeff Chisum: 100% of my business is helping clients in all 50 states with purchasing vacation homes/STR properties. 90% of my clients use the 10% down second home occupancy loanIf you want help with understanding loan options and what could work for your situation, get ahold of this guy asap!