Hey these are awesome ideas! Haven't changed the plan yet, still noodling over it all. I agree with your points. We're treating this as more of a prototype / MVP / test the waters. I think we're going to proceed with the free plan (similar to your idea), and in meantime (in the SHORT meantime) reach out to charities and some big stars to see about seeding / cross promotion.
Cool, it sounds like you're taking the right approach. You can use what you learn for next valentines day. You could even do it for Xmas (leave a present under the tree for someone you love)