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I can't get my checking account to reconcile

HI there - I have used Quicken on my Mac for decades (really!!) I have religiously reconciled my checking account every month to the penny - but back in December 2019 I noticed a discrepancy - thought I would be able to sort it out the next month so I held off on reconciling in December. Then January was worse, February was even worse and now its time to do March .
I have tried to find my error to no avail - I've deleted all the transactions back to December, re-entered them (yes I still do this by hand each month) I cannot figure out where my error is. I've even worked with another person who has double checked my work - so now I have a mess on my hands - because I can't figure out how to move forward - each month that goes by stresses me out because I have a different balance on my register than I have on my bank website. I don't know what to do
I think it may be related to a change in the software (I noticed a change in how my entries looked in December 2019) and transactions that the software remembered weren't functioning like normal - When I went in and deleted all my transactions I went back to the last time it balanced. But then after entering the transactions again I can't figure out how to begin reconciling because the beginning and ending balance don't match my statements anymore.

Does anyone know how to proceed?

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