However, one of my biggest concerns when fixing homes is knowing when to use permits.

I understand your concerns and anxiety about getting started as an OOS investor when trying to choose a good market.

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

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.

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. 

That's great that the bank who currently holds the note wants you on 20 year or 15 year amortization, they view you as a captive customer, they don't have to earn your business any more, as far as they are concerned. 

There are other concerns with this approach, but 50% down on a ready to go $150k rental in a cheaper area?

I understand your concern it’s always important to ensure everything checks out.

They remain available to assist investors throughout the investment lifecycle, whether it involves refinancing options, addressing financial concerns, or facilitating future funding needs.

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.