Kent,Since you have a good relationship that's probably the best route to go in your scenario. 

Maybe I haven't found any of the "good ones" yet and I realize that any good deal that comes my way, no matter what route, is good.

If so, please DM me and if I decide to go this route, you'll get a little something for helping me out. 

Before you start comparing, pull up a google map and just look for 30 seconds... what are the natural indicators (major roads, intersections, etc); take a quick look at topography, is there a ditch or a river that runs in a certain spot?

I have a feeling the next house will probably be bought with conventional financing through a realtor but I'm trying to figure out how to build relationships in the area so I can move away from tradition routes.

If I did go this route, would I need to get an attorney's office to handle the paperwork and escrow?

Many distributors have a Route Program where they install the machines and collect the money and service them.

If going the financing route the lender is going to want to see the buildings income  expenses.

You can potentially get better lawn care rates, PM rates, maintenance, etc because of the efficiencies the density of your properties all in 1 spot allows.I'm by no means a baller but you don't sound like someone who wants to dip a toe in... you're talking about dumping $300k a year into real estate... so if you're going that route, all in... go big or go home.For most people I would say buy 1 property, wait 6 months to see what you missed in your first deal, and then move forward... but most people don't have $300k in liquid capital to dump... most tie up their entire life's worth in that first property.  

I don't really want to go the low income, government subsidized route.