Automatic Membership Renewals

Before I do to much digging, I wanted to see if anyone does automatic membership renewals via the web. I know that there is a utility report in Tessitura reports that can do automatic billing, but will this work in conjuction with the web? More specifically, will I be able to send emails notifying people that their membership will expire in say 30 days and that we will automatically renew them. Then if the billing fails, can an email notify them of the problem. Automatic renewals is becoming more standard with web based services, so my boss wants me to do this for our institution. Fun, no?