., I would take @Daniel Moffett and @Nathan G. advice.Always follow the regulations and be prompt on your notices. 

I agree with @Jonathan Greene- off market deals are bought with cash, less contingencies and established investors.

Less regulation is the way to go and leave it up to the landlords to make their own rules.

Lesson learned: The cost of the money was irrelevant to the value of trust that was established in this deal.

I’m not in a place where I feel like I need to worry about tax avoidance (I probably can’t beat the standard deduction yet), but I would like to find a tax professional / CPA and establish a relationship as I start investing more.

Maybe he should just sell you the real estate so that you can establish the proper cost basis.

Typically, people stay in hotels or other lodging (AirBnB/VRBO) but I wanted to take a different approach.I would be looking to purchase a duplex with the intent to finish the basement and either convert to a full triplex if allowed or keep it as a duplex and rent out the basement separately.The Joint Travel Regulation (JTR) states that a member is not authorized lodging reimbursement if the member purchases or already owns a property that is used for lodging during official travel.It’s clear that I won’t be authorized reimbursement if I purchase the property under my name, but what if the title is under my LLC with me as the sole owner and rent out one of the units (probably the basement) to myself? 

Lastly, do I need to set criteria and inform him of my criteria BEFORE screening him, per fair housing regulations?

For the out of state strategy, we established a network.  

You should have an established, written policy to follow.