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One of the concerns I have for my children, especially my oldest is that I think I want them to have success  more than they seem to act like they want success.

If you’re concerned about paying personal capital gains tax, remember that flipping the property means you’ll take the profit all at once, while with BRRRR, you can defer some taxes and have the property generating income.So, here’s what I’d do in your shoes:If you can make a decent profit flipping and then use that cash to roll into your next investment, you might be better off taking the cash, at least for the first project.

As far as the garage concern, it was not included in the lease. 

Quote from @Kobe Carr: Looking to get started with real-estate and would Dallas Texas be a good start for a beginner  Where do you live?

If you are truly concerned with liability, these should be your main concerns and focus, not whether to create your LLC in Wyoming or elsewhere. 

I guess my main concern with the Tulum area is it seems there are soooo many new developments going in (an agent told me 151 new developments over the next 4 or 5 years), I think the competition for vacation rentals will end up like Playa del Carmen (saturated and cut-throat with competition).

Assuming your family is shielded from your risk, the quickest way to do it would be to flip homes, but I would not recommend that for a beginner.

Kissimmee is still a strong STR market, especially with Disney nearby, but competition has increased.The smaller pool and backyard might be a concern for some guests, but the privacy from the freeway could be a nice bonus.