Do any of you on TNEW upsell a single-ticket purchase to a flex package?

Hi all.  We are on TNEW and we want to start upselling from a single ticket purchase to a flex package.  Do any of you do so and if so how?  Pricing rules came to mind and I did some testing with a message-only rule and it was very clunky and not user friendly.

Thanks!

Heather