We are prepping for the release of a large web application that has been in development for the past year. We are about to start the process of integrating ActiveMerchant to han
RailsKits has a Software as a Service kit that should do what you need. It has built-in support for free trials, upgrading, downgrading, plan limits, etc., and it supports PaymentExpress (and some others).
I've researched it a bit for a project I'm doing, but I haven't purchased it yet so I can't vouch for it. However, I have seen a few blog posts praising this kit.
While the RailsKit is relatively inexpensive when compared what it would cost you to implement all of its features yourself, there are a couple open source versions out there that aim to accomplish the same thing. The one I remember off the top of my head is called Freemium.
EDIT: I forgot to mention that Ryan Bates said in his most recent Railscast that his next episode or two will deal with recurring billing, so keep an eye out for that. He usually does one episode per week, and the five he's done since December 22 all cover handling payments of different types.