This is a personal choice and depends largely on your risk tolerance level and the current demand for rentals in your area.Vehicle Repossessions: Having a vehicle repossessed is strong indication that a tenant cannot handle their money very well.

.: It's not an issue IF their lease is scheduled to expire.My personal practice: when a tenant submits an application, I let them know I intend to contact their former landlords.

If someone injures themselves and sues, they will be suing the LLC and not you personally.

Personally I don't think this lends itself well to the fund model. 

We have an LLC that holds real estate but have run into issues refinancing through the LLC when family is renting or ultimately living in the property so I’m also not sure if this should go through the LLC or be a personal purchase?

Imagine turning your investment into a personal getaway when it’s not booked—sounds way better than a condo-hotel in Vegas, right?

Need some advice on the best way to structure this deal that's fair and beneficial for a 3 person LLC/partnership agreement. 

They will try to run 2 kitchens and that can mean clogged drains in your wet bar kitchen.Be sure there is personal recourse when you need to sue them for $40k in repairs above the deposit.

You may not get the first property you offer on because if it looks good to you, you will probably have competition so start offering on properties that fit into your personal investment philosophy and meet your minimum financial requirements. 

You might want to limit your visits though to avoid escalation.Short term if the smart lock is on his personal door just change it to a key if it's isn't working for him, you can always switch back later.