I'm ready to take a dive and be comfortable being uncomfortable.

My number one advice would be to separate out those who "Want a Date" types from those "Want to invest ONLY to make money".Mix those strings up and things could get very complicated and uncomfortable--b/c you know some of them are out there.What I'm saying is try to keep business and personal as separate as possible.Just my 2 cents.

It may be uncomfortable, but it is necessary for a successful partnership.Whatever you decide, you will want to put it in writing and have a partnership agreement written up by an attorney to ensure it is legally binding.

You should outsource what you feel uncomfortable with to an experienced professional such as a property manager.

However, with all of that said, I do not feel uncomfortable in today's market with a loan.

Some tenants in my experience don't care and if they are offered money to move they will be packed by the end of the day and others were not wanting to move because they have a routine that they don't want to break. 

Routine inspections while a tenant occupies the property can be conducted every three to six months and will allow you to stay on top of maintenance and address any issues with the upkeep of the property.

We don't go to every routine plumbing call or no heat call at this point, but we keep detailed notes of how the mechanicals work at each building so that we can trouble shoot virtually. 

Protect both parties from the what ifs to avoid some uncomfortable situations down the road.

Personally, I would be uncomfortable with the wording as is.