I agree they had communication issues during a transition period that we dealt with, but things have improved from last year. 

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

The seller is not very tech savvy and is going through some life issues so he isn't being very helpful in this.

Anyone else having issues?

Unfortuantely, things happen that are out of your control.The insurance issue is such an important takeaway.

Any insights from your experience, whether positive or negative, would be greatly appreciated.The attached link explains the current situation with the Detroit Housing Commission (DHC), highlighting that they are severely understaffed and have limited communication with both tenants and landlords.

That’s our primary method of communication so it works.

With the income issue, there are screening systems available that verify income by having applicants securely log in to their payroll provider, which then shares their gross and net income with you.

@William Causey depends on the transaction and the parties involved.Agree with @Dennis McNeely on some of the transaction costs.A different issue though is with an Assignment, the buyer gets to see what you paid for the property.

Keeping your license and avoiding any legal issues is probably worth more than this one transaction.