@catonh @bovineyard 

You are using QB Desktop with a non subscription license. I didn't see any specific reason why do both of you have to upgrade to QB Desktop 2024. Regarding 1099 contractors,  I can share a stand alone free billing management app to manage and pay your bills. It provides a downloadable CSV file of all your payments so you can view, classify, and export your payment history to prepare your 1099 report manually. Then you can use a free tax filing service app to proceed.

Contact me in private for details.