Ecommerce Club solution?

I have a client who wants to offer 6-12 month widget-of-the-month clubs. There would be several different packages to choose from, and they would be able to make some selection within those packages, and each item can be personalized (think – engraved). Then they would be billed monthly for 6 or 12 months for their membership in the club, and the items would be shipped out monthly.

I think WP Ecommerce with the WPEC Personalize plugin are the way to go for the personalization part, but how to handle the club subscription?

Thanks for any ideas. Also interested in outsourcing this, so if you can customize a plugin or something that would do this, give me a ballpark figure!