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 and dial-up transaction downloading became available) 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 each payment directly from my checking or credit card account on due date. Now I can sit back, relax and wait for it to happen. Instead of having to wrestle with making payment on time I let the biller do all the work for me.
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.
I recommend you do the same instead of fighting the Bill Manager windmill, missing payments and getting slapped with penalty interest rates or late fees.