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It takes some work to find the right candidates in the service drive, manually.  But if you can get in front of someone who would be interested in receiving a package of information about what they could trade their car for, you may be able to get more bites.

Hang out in the service drive and ask people if they want to know what their car is worth.  Assuming your used car manager can give you a guide on how to give them a quick number you could do it on the spot and then ask if they'd like to see payments on an upgrade.  If your manager isn't comfortable with you giving a number on the spot, find out how your manager would like you to give him a condition report.  After presenting that report, he should be able to give you a range he's more comfortable showing a customer, and you could call/text/email that range to the customer.  Then ask if they're interested in exploring payments on an upgrade.

I wrote a white paper on how to mine the service drive a while ago.  There are some talk tracks and email templates at the end.  Maybe it will help you:  https://frkn.tech/ToolsToEquityMineService