Pretty interesting to cast doubt over my reputation/character when (A) you don’t know me and (B) unlike everyone else, your assessment of the conversation went in a direction that nobody else was going towards.

Of course, we will be having our local lawyer take a look at the lease.I'm hesitant mostly due to the overwhelming legal power and experience that this tenant would have compared to our small LLC.

Telling them too much they will start throwing what "you're supposed to do" in to the conversation....whether that is accurate to this specific case or not.As far as the parcel segregation, you could actually apply for that any time in theory.

I would love someone to see if they can have a conversation with him and let him know that I'd like to give him an offer.

I see your point about working for this investor as a way to learn and potentially have conversations about acquiring his properties later.

I would just take a look at their list before you start the eviction process and have an honest conversation with them.  

@Luke NaylorThere is some high powered PM software out there, but those are typically not a good fit for buy and hold investors with your size portfolio.

I'd highly recommend having a phone conversation with a few agents to see who you get along with, and also can be on the same page with. 

My wife is concerned about not getting the return on this expense, and she agrees with Carson regarding power-washing/cleaning and repairing the driveway. 

Require proof of funds earlier in the conversation.