My friend recently told me of this scenario where the person I lease to would perhaps then double book individuals and keep deposits. 

In-person showings just aren't efficient.

You are AT LEAST 10X more likely to do something personally to get yourself sued than your property is.

If you and your partner are in it for a long term buy and hold option I would recommend purchasing homes in your personal name then quitclaiming to an LLC.

Did the lawsuit show up on a personal background report?

You may be able to factor in certain improvements to your personal residence so when you do move out, you can be eligible to depreciate it.

Real Estate CRM software stores organized data about leads and customers, such as personal information, communication, and purchase history.

From what I have researched they seem legitimate but the person I am working with is flakey, takes forever to answer questions so I thought I would see if anyone else had experience with this lender.  

I personally wouldn't buy a 2 bed house for $100k all in in Detroit.

One thing I have also seen investors do is have too many personal use days which can have lead to a similar situation as Jackson.