C+ Neighbourhood13 Unit Apartment Building (Link: https://www.loopnet.com/Listing/7828-S-Essex-Ave-Chicago-IL/30374409/) The average Rent is $1400-1500 (to be safe $1300, but I am extremely confident that I will be able to rent higher adding value and convenience to the tenants and treating them as a bit with a higher level of service) - $16,900 at full occupancy and ~$12,000 at 70% building. 

On another side note, I thought what I was charging him was fair as it covered the mortgage and minor repair costs.

not positive but ballpark guess not sure how much those cost yet... but im using the 70% formula so   364,080 x 70% - 30k (repairs) - 8,500(whoelsale fee) and i get $216,356 as my (MAO).

Tell AirBNB or VRBO and get them to work on the payout for the repairs.

They are priced under market value, no major repairs, really only need updates. 

And I’ve thought about doing the 50% down method because at least you still get to have the tenant pay down some your debt service.

Sheriff service is $50.00 per defendant, if you request it.

Is there a service that can help me or someone willing to walk me through what I need to do? 

I'd love to put you in contact with these people and start marketing your services to them, I have done this maybe 40 times now with my current lenders and i typically just add my payment into the HUD and the borrower pays it, this service wouldn't cost you anything.

I own BlueRibbonHomes, a full-service brokerage that includes property management.