Any advice on the process above would be greatly appreciated.

After discussing their goals, we realized they would like to maximize the property's value while also including me in the process, given my background in general contracting.

I am in the process of getting a HELOC on my primary residence at the moment.

Does anyone have any other tips and tricks for helping out the appraisal process so I can get the best out of the situation. also what what other things can I put in the folder to give him or what you've done in the past?

Because the payment is coming from the tenant, and not the surety bond provider, claims are always processed without a fight.If you are interested in considering a surety bond program, I recommend Obligo.

I'd have them sign my own lease on renewal and I'd make sure I had enough information on them so I can go after them if a legal issue arises such as employer and other similar data. 

I am admittedly a newb in the process of getting all of this set up for my first rental (so correct me if I'm wrong) as well but I have some IL-specific perspective to offer: From what I have read, as of 1 Jan 2024 in IL, landlords cannot exclusively accept EFT payment of rents (includes Venmo, Zelle, etc.) for leases starting on or after that date.

I'm moving to San Diego next year from Denver, CO and am looking to make the right personal finance decision in the process. 

We like to stay in control all through the process..

I know you've learned a lot through the process.