Looking for some advice on upgrading

System

This discussion was created from comments split from: Quicken Bill Manager - what are the limits & fees for Quick Pay & Check Pay?.

jtoussieng

Quicken 2017 vR19.8
Looks like for whatever reason I got an email that says my Deluxe has been successfully activated on 3/5/20 and will expire on 3/5/21 even though when I did the download from the email I got a pop up telling me to open Quicken and go to something that did not exist and enter my card code. So I guess it just rolled over without me doing anything.
I am not sure if I should stay with 2017 or upgrade.
Regarding Bill Pay that was a part of my question easier to purchase as it upgrades to 2020 and I believe includes QBM. Not that i need any additional things in Quicken. Since I am not an annual pay member will I be able to continue to use 2017 indefinately without having to renew at a cost every year? If not then upgrading might be necessary anyway at some point.
Just trying to get some advice. Scary that when it installs it removes the current Quicken. Again, based on past experience with issues and the issues I have been having for a few years that I have learned work arounds for, changing is scary. But maybe it might be smooth.
I do wonder if the issues I have been having; Entering a payee from the list and it populates a very old last used check. It never resolves to the last use, so I have to always edit it to the correct information like tax category, memo, etc. I also have to use CtlB for back up because when I select it from the menu it changes the order of payments in my register and ends up very much in the red.
I have made phone calls with tech support who have not been able to resolve and have done things that have created duplicate and more entries of the same thing in my register.
So maybe whatever is keeping the payees from being current to the last entry might be embedded in my file somewhere and changing to an upgrade, which I have done anyway a couple of times in the past few years, won't fix it. starting from scratch will take me days.