Coaching site - Module help

Hello everyone, I've been messing with Drupal for a while now but just recently a client came to me and asked me to help him setup a Coaching site. He had a site somewhat setup that I was helping him with but a problem with the host and their CMS led him to abandon it completely. I suggested Drupal but to be honest I did not completely know if it was possible.

So here are my client's needs.

It will be a coaching site, so there needs to be a signup system (already included in drupal which is great) and then if they like what they see they can then pay for membership. Heres where it gets difficult.

The visitors need to be able to pay for upgraded membership. Is there a system that allows this? I know there are modules for this but the specific issue is that he is using 1shoppingcart.com and does not want to change. How can I use this site to pay through?

Once they are a member they will gain access to all the membership stuff but the client wants the items to be delivered on a timed schedule so say a video on day one then a report on day three and so forth. The members will not see the upcoming content until the schedule says so. Is this a built in function of drupal or is there a way to do this?

Right now I am really interested in CivicCRM and have been experimenting with it. I am also looking at the premium module and Ecommerce. Has anyone built a site like this and know what works best or are there any recommendations?