@Robert BelzMuch thanks for the experience based advice; will be incorporating it into my plan.Jesse

I would likely conclude that your failure to disclose arose out of putting your economic interest ahead of the tenant's physical safety.  

Property, benefits, and rights are included in real estate.Clearly, the property is permanently attached to the physical surface of the real estate, what is above and below it, as well as to all property rights, including the owner, seller, lease and enjoy the land.

Gift tax has me concerned, and trying to research the best way for him to physically invest the capital of the upwards of $75k in our first investment.

I would talk to and physically look at their last 3 jobs.

That said, he is very supportive and also has a tough and physically demanding day job, so I can understand why he doesn't have as much energy or enthusiasm for this as I do. 

-For the right person/couple, potentially extremely reduced rent + $ in exchange for some physical labor and administrative/management duties.

That way I can spend time learning that market first hand through physical exploring and having conversations with big players (agents, brokers, investors, etc) and also build my team.

We have a very long list of items that we look at during DD that includes both the physical and operational sides.

Underwriting needs to incorporate everything you know about the property.