While I'm not a lawyer, and I know that's the focus of your questions, but I have other concerns about this situation:How long it's been going on?

@Jo Ballagh  You have an interesting situation that is probably not specifically addressed in the law. 

Addressing the problems is like trying to put out small individual fires in a forest that is burning.

The only concession I got from him was (1) He and all crew members will sign a hold harmless release of waiver of liability form in case any of them got injured, and (2) cash means I will write him a check in his personal name.So I do have cancelled checks to individual names, even on the check I wrote a reference "debris clean up @ address". 

Every concern I raised they were right on it and I believe their pricing is fair.

The agreement can be as simple as to say the 'property owner A' and property owner 'B' hereby acknowledge the proximity of their respective driveways and affirm that neither property has any easement right/necessity over the other.The concern here from a lender/title perspective is the ability to claim a prescriptive easement right.

That is correct, anything that is not on the contract as an exception if you purchase title will be addressed."

another thing is contacting a local property management company and asking them if there are renters looking in the area you're concerned about. 

What happens if they are concerned about DTI?

If that is the case, there will be two addresses - the property address and the mailing address - both on listsource and at the county.