., unfortunately, to add to the frustration, Buildium's journal entries do not allow you to enter a vendor for the expense, you can only select which GL Account to debit and which payable to credit, so I'd still be stuck not able to track vendors for 1099's, see below.  

Outside of that, I am in a lower barrier to entry market of Cincinnati/Northern Ky.

Kudos to you for doing something to create a secondary income stream. there are 5 income streams in RE rentals, possibly six if you do things a certain way.The reality here is your model (buy box) is suffering from too high an entry and too high a cost of capital.

This is a small 3 br house.Work Order Instructions:- Entry 1 : Security/Screen Door | Replace Exterior Door Screen- Entry 1 : Wall/Ceiling | Spackle and paint- Bathroom 1 : Door Stop | Replace door stop- Bathroom 1 : Light Fixture | Replace bulb- Bathroom 1 : Shower/Tub Caulking | Re-silicone tub- Bathroom 1 : Toilet bowl/lid/seat | Replace toilet seat- Bathroom 1 : Toilet Paper Holder | Replace toilet paper holder- Bathroom 1 : Tub/Shower | Relay loose shower tiles- Bedroom 1: closest to the front door : Closet/Door/Track/Shelving | Install Closet Rod- Bedroom 1: closest to the front door : Light Fixture/Fan | Fan light does not work - replace fan- Bedroom 2: 2nd closest to the front door : Closet/Door/Track/Shelving | Replace closet rod- Bedroom 2: 2nd closest to the front door : Window Covering | Replace blinds- Bedroom 3: furthest from the front door : Switch/Outlet | Install smoke/CO detector- Bedroom 3: furthest from the front door : Window Covering | Replace blind- Dining Room 1 : Window Covering | Replace Blind- Hallway/Stairs 1 : Light Fixture | Replace bulb- Hallway/Stairs 1 : Other | Replace blind- Kitchen 1 : Window Covering | Replace other blind- Laundry Room 1 : Light Fixture/Fan | Replace bulb- Living Room 1 : Switch/Outlet | Replace Outlets- Living Room 1 : Window Covering | Replace Blinds- Basement 1 : Light Fixture/Fan | Replace bulb- Systems 1 : Thermostat | Reattach thermostatLine ItemsDescription AmountLabour hours, replace several blinds, screens, door stopper, replace toilet seat and toilet paper holder, reset showertiles, install closet rods, replace necessary bulbs, smoke detectors and outlets, touch up paint$2,096.38Shop Supplies $3.00Ace hardware invoice I51016 $44.64Ace Hardware I50619 $53.69Ace Hardware I50569 $43.57Total $2,552.16The gross rents on these units are great but so much of the profits get eaten away by the turnover costs it just makes less and less sense every year. 

The “students” in these programs, for the vast majority, have none and receive none of the above base requirements for a successful entry into the field.

(For a lot of gurus, the education is just a top of funnel entry point for them to then have you find deals for them, invest in their deals, etc)If they are active in real estate themselves, I would ask how much they are making from their RE versus their courses?  

It is required the Property Manager return all personal property belonging to the Owner such as keys, entry codes, copies of lease agreements with existing tenants, tenant deposits, and any other files or information necessary to manage the property and the tenant(s)."

Wondering what the best entry point would be.

That would be the lowest barrier to entry in most scenarios. 

Do this for all items and include an entry for small items like lights to get cap ex estimate  Not sure where you got the 3% vacancy number.