Last thing I wanna do is battle the city but can’t swallow paying this much money either lol.  

I personally would pay to skip the line and condense time. 

Is it worth paying the fees for each stay and getting a long term renter or is it better to keep the reservations? 

Pick your dilemma - tenant quits paying rent and squats in the house for 2 months while you spend $1,000 to evict them, the AC goes out and it's $5,000 to repair, you need a new water heater, or roof, etc.  

The payment standard is what Section 8 will pay UP TO, but beware it does not  guarantee they will pay the top amount. 

The goal would be to refinance after 5 years, use appreciation to pay off 60k, and cash flow would continue to increase over time. 

Take ownership of your mistake and learn to do the proper due diligence recommended above😊

The guy messaging me says he will be the primary person of contact and be paying with a credit card for payments.

What do you pay that poor guy?

Assuming you're not an arborist, you made a judgement call regarding someone else's property and now you are going to have to pay the piper.