Like Caleb said, I'd look at them individually as though you're doing each on their own.

We took a 5 unit building that had one electric meter and one 40 gal water heater and separated them individually and had the tenants pay for their own utilities.

I am not looking for any handouts; however, I would like an individual or community to connect with to help me consider things that I otherwise wouldn't. 

The general rule is that an individual is an independent contractor if the payer has the right to control or direct only the result of the work and not what will be done and how it will be done.Since I'll be investing remotely I'll be requiring someone to help me out in the "bird dog" activity of finding properties through driving for dollars.

This is common of all the "pop up" tax preparation companies.There are also other classification of qualified individuals who prepare taxes.

There is a big difference from a title company holding earnest money funds in a secured account vs an individual person holding those funds. 

My confidence grew exponentially once I started being around like minded individuals. 2.

If he passes the screening and if you don't want him on the lease you could make him an "authorized occupant".

It would be really cool to connect with other individuals in and around my area as well! 

Freddie/Fannie guidelines prohibit lending to entities (the borrower must be an individual) and you will get the best terms with conventional financing.