Can this be done? MailChimp + Membership drip campaigns?

I'm trying to launch a two-tiered membership/email autoresponder system. People can sign up for free and get a brief bit of info via my email autoresponder (preferrably run on MailChimp, but I'll consider other options). At the end of the info is a link to a post that is behind the membership system.

I don't want people to be able to get ahead of the content if they're paying members (pretty sure that's easy to do with Membership).

I want people to be able to upgrade at any time and see all of the old content.

I guess my main question is that if someone gets the freebies up through #9 (just an example), then decides they want to upgrade and go through the Membership payment system, will they get lessons 1-9 to start off and the ongoing lessons in sync with the email newsletter?