These are the scenarios I'm looking at.Let's say the three parties (Me and my wife, friend, and sister-in-law) invest three ways, say 2:1:1, with the friend being the biggest investor.

My brokerage is part of Anywhere RE, we have the biggest names under our umbrella (ERA, Caldwell Banker, Sotherbys, BHG, Century 21) and we have a fantastic referral program that I can hand pick an agent anywhere in the country and interview them for you to make sure they have the qualities you are looking for.

My biggest concern with house hacking is giving up my primary residence.

This may be because (1) until recently interest rates were trending lower so if the lender is getting a higher rate on subject note than he can obtain on new note there’s no monetary incentive to call the note (2) in the past technology did not exist to identify the property transfers (ten years ago county recording docs were not online) and (3) the lenders rather collect payments than own property.  

While your lease may indicate that the tenant pays, the biggest problem with this is that tenants will stop reporting issues for fear of paying.

The one thing I do not like is that you cannot serve him personally which is for me the biggest hurdle.

I would also look at employment/unemployment statistics, and get a good sense of who the biggest employers are in an area. 

But for me, the biggest shift was developing a routine and using tools that let me see my rental finances at a glance.Anyway, that’s my two cents.

The single biggest issue in my way currently is obtaining enough cash, whether it be my own, or through partnerships or family/friend-based lending (which I am very hesitant about to begin with as this could potentially strain relationships unnecessarily when money is involved).

I also love your take on creating incentives for property managers.