I'm sure there will be others with their own (and possibly conflicting) opinions, but for question #1, I always advise my clients to focus on properties in areas that 1) they currently (or previous) live in/near, 2) they travel to frequently, or 3) they have family/friends in the area.For question #2, the answer is going to depend on what you do for #1.

I definitely don't recommend renting to a friend.

I was hoping someone had a referral for an investor friendly attorney who can help with contracts specifically dealing with wholesaling both MF and SF.  

For any locals that come across this or virtual investors , what's a wholesale friendly title company you've worked with in St.

This triples your headache.BE the voice of REASON to your friend. 

Rodrigues' recommendation may change this), but my next question would be, are there any cities/markets where 1 of the following are true: 1) You have family/friends that live there, 2) You travel there frequently (either for vacation, work, etc.), or 3) Somewhere else you've lived before AND know the area well?

Besides a declining population and tenant-friendly laws, you have to deal with the fact that neighborhoods can be as small as a city block in many cases.

See who represents owners frequently in your jurisdiction and get set up with them.

We want to get a few rentals up and running and then (if all works well) begin bringing other friends/investors in to invest with us.

@Jerry Maze What do you mean by investor friendly exactly?