And finally, if your being honest, you're terrified and would absolutely be medically diagnosed with analysis paralysis. 

We fell into a dismal financial situation in NYC (medical bills, costly immigration fees, snowballing living expenses...) and decided to move to Tucson where the cost and pace of living is more manageable.

To deal with short-term rentals by hotels and other similar businesses,  the states simply exempt them from these licensing laws if they have a legal hotel/motel operating permit.

@Gabriel GrahamWelcome Gabe - have you thought about the types of investments you'd like to pursue, ie residential rentals, commercial or perhaps even more specific medical office which I'd assume you already may know a lot about given your dayjob?

Because the "owner" of the LLC is your IRA ( a tax exempt entity) there will be no taxes due. 

Plus I didn't have a home exemption so was taxed as an out of stater.

I just finished my studies to become an emergency medical technician.

I am wondering, if I kept some of the proceeds out to help pay for my dad's medical bills, would I pay taxes on the entire net amount from the sale, or simply the amount I keep?

I will be buying a plane ticket on my 18th birthday to come to the US, and get a degree with the hopes of medical school, and an eventual career in anesthesiology.Ideally I want to take on a few mortgages, and pay them off with rental income from those properties.

It sounds like from what you described you are exempt from Dod frank if you only do 1 per year.