About your Bill Manager issues
My 2cents' worth, if I may: I don't use Bill Pay services or Bill Manager at all, neither the one from Quicken nor the one offered by my bank. Since time "B.I." (before the Internet was invented) I have set up almost all of my recurring payments as Direct Debit, PAC Draft, Autopay, APS, whatever the biller calls it. Using the biller's website, I authorized the biller to electronically debit the payment directly from my checking or credit card account on due date, sit back, relax and wait for it to happen. Now instead of me having to wrestle with making payment on time I let the biller do all the work.When I get notified of a new statement having arrived, usually by email, all I have to do in Quicken is to run a regular scheduled reminder to record the transaction. Haven't missed a payment in many years.