I pay a neighbor's kid $10 a week to roll 2 cans down to the street and back. 

I purchased a property in Chicago in 2024 and pay $400 a month for my water bill (unmetered).

Going DIY and self-managing this type of asset from another state may not be an easy task for such a building and neighborhood, it needs more attention (and probably capital).Try an unconventional approach.

That's the maximum amount we will pay for the note.

. - If I pay property taxes online (let's say with a credit card), will my name show up as the payor or will the trust/trustee's?

Contract for deed seems ideal as you could be making payments to him, which helps him pay the mortgage and extra for his apartment/travel.

I never pay MLS list price.

What are options for having our investors pay their share of this monthly fee?   

Let's say you're paying 3 points and 12% to a real shark. 

They don't pay the same taxes a citizen would pay.