I also think of property locations and property conditions having different classifications. 

If you're located in WI, check out Premier Point Realty and Homestead Realty....both offer the licensing course at a discount and some of the lowest fees/commission splits in our local market.

Hi all,I'm looking for recommendations for a property manager for my 8-unit apartment building in Cullman, AL.

Your property management company can help once you own the property but up until then you need someone good on your side!!! 

He get's principal and simple interest payments over a number of years.I'll manage the deal and the property.Looking to create a proforma for this that would fit a typical rental analysis but insert the detail of having private money cover the DP.

My plan for this year is improve my credit, get my real estate license (to increase my income on top of my W-2), possibly career transition into the property management space (to learn more), and save as much as possible and learn as much as I can.I’d love to house hack close to home but my area is so expensive it seems like it’d be close to impossible. 

Are they way under market, or is it manageable for now?

You just need a good property manager.

Quote from @Kevin Brown: Hi,We own and manage two AirBnb's. 

Pick 2-4 locations, get no more than about 6 deep in any but no less than 2 deep.