Hi there, @drupedrupe. I'm here to guide you in paying multiple bills with different dates in QuickBooks Desktop (QBDT).
Thanks for sharing detailed information as well as screenshots of your concern. Let me discuss some details on how you can perform the process.
With QBDT, you can only pay bills by batch if they have the same payment date. That said, you need to make separate payments for those bills with different payment dates. Here's how:
- In your QBDT company, select the Vendors menu.
- From there, choose Pay bills.
- Next, select the checkboxes of the bills you want to pay from the table that has the same payment dates.
- Then, input the date you paid the bill in the Date field.

- Fill in the needed details and select the Pay Selected Bills button once ready.

For reference about the process, feel free to check this article: Pay bills in QuickBooks Desktop.
Monitoring the total amounts you paid to a vendor for a specific period is a breeze in QBDT. To do so, you can run a Transaction List by Date report and customize the data.
Please get back here for updates on how the steps go. I'd appreciate any details you can provide. If you have any other questions about paying bills in QBDT, simply leave a reply below. I'm always ready to lend a hand. Have a great day ahead and take care.