Welcome to the thread, schultz2020.

Thanks for providing detailed information about your concern. It was super helpful, and I feel like we are on the same page.

At this time, importing transactions in PDF format is currently unavailable in QuickBooks Desktop (QBDT). As a workaround, you can search for a converter online. Once everything is set, you can import the file to QuickBooks Desktop.

As for converting Quicken files to QBDT, you have two options to start the switch. It could be converting directly to QuickBooks Desktop or use the Quicken converter to upgrade your file first. For more detailed information, you can take a look at this article: Convert Quicken data to QuickBooks Desktop.

For your last question, have you encountered any issues in accomplishing the OCR using the Money Thumb? Can you provide additional details for me to give the right resolution? 

Moreover, I don’t want to leave you empty-handed, you'll want to visit our Community Help Articles hub in case you need some related articles in managing your account.

I'll be looking forward to hearing back from you. Have a great day!