I should just give up on the pursuit of self-improvement and fall in line, so I don't hurt peoples' feelings and make their childhood trauma of feeling discredited and unheard flare up."

As the saying goes, "in a gold rush, be the guy selling picks and shovels".

Plus you're just blasting people that have already gotten a ton of blasts before by now.Remember that adage about the ones making money during the gold rush were actually the shovel sellers?   

Step One: Gave them a taste of entrepreneurship (rite of passage stuff) they cut grass, shoveled snow (as a group) Team workThen my wife an I let them try their own ideas out on the world.

A high quality SFR in Austin will pay dividends in the long-run, and don't invest for anything but that. 5-6 years is too little, but if you are to expose yourself to that I would still take Austin.Those deep parts of SW FL are cyclical with retirement up & downs on economic recessions.

I'd never buy a development unless I was confident in the valuation and there was data to back the feasibility of the build. having preliminary approval is very different than permit ready where you can put a shovel in the ground day one.

They also mow the lawns, shovel the snow, pay most if not all utilities, and provide most of their own appliances. 

I'm an insurance broker and I agree rates in FL are insane right now.

There is money in buying raw land and getting it permitted for build with plans and flipping it shovel ready 

The project is shovel ready.