Tom Young said: My approach is to not use the Quicken system but instead use the check (or ACH) issuing feature of my own bank.
About your Bill Pay / Bill Manager issues
My 2cents' worth: I don't use Bill Pay / Bill Manager at all. 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. Just authorize the biller to debit the payment directly from your 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.