Hello @Chuckster
Thank you for reaching out to the Community regarding your issue, although I am sorry to hear that you are experiencing issues with your data file. I'm wondering what is causing the issues as they sound like they have been fairly consistent. One step we can test here is to see if we create a copy of your file and connect your banks back if we'll experience the same error. You may want to only do a couple of banks to start to see if they still experience a similar issue. I'll leave steps down below on how to create a copy. You'll find it on the fourth step in the article.
https://www.quicken.com/support/advanced-data-file-troubleshooting-correct-problems-quicken-windows
Once you get a chance to try these steps, please let us know what you find. From there we'll better understand our next steps/options.
Thanks,
Quicken Francisco