About your Bill Pay / Bill Manager issues
My 2cents' worth, if I may: I don't use Bill Pay / 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. I just 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.
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.