The claim is put before an arbitrator who determines the percentage liable. 

I am in the process of getting pre approved for a loan and I’m curious whether or not I have to claim the debt on a rental property that I bought using  owner finance.I realize it is somewhat a grey area but from my perspective, it seems like it would be private debt and would not show up on the bank side so there is no need to disclose it.Furthermore, my bank already ran my credit check and said the mortgages did not show up. 

I know you sort of made up the numbers in your post, but making $1000 for an hour of work each month seems unrealistic. 

My background is on the claims side of the insurance world, but I'm a little confused about our circumstances.

I imediatley follow claim with insurance company. 

My snow removal company only salts, no sand and given the cost I was going to switch companies but then realized in my northern climate it’s just worth the extra cost to have it done and over with especially after a tenant claimed a late spring slip and fall last year.

I may just have set personal expectations that are unrealistic and need to adjust and focus on lead measures.

(They wanted to replace the deck in the back with a paver patio since they claimed the deck was unsafe... not true, but I'm getting a new paver patio and full asking price so we said okay). 

Do the two partners put a JV agreement together, and then one person buys with conventional in his name, and then both partner's LLC's are added to title via a warranty deed and/or quit claim after the fact?

In case of a property or liability claim, it goes in their records, not yours2.