1. There would be 3 types of membership plans, eg Level 1, 2 and 3.
2. Restricted areas accessible only to members. Is there a way to control the contents available only the respective membership level? Eg, if a user signs up for Level 1 membership, therefore only level 1 contents will be made available? Does CB allow this to be implemented?
Both can be done using CBSubs.
3. Members' personal area where they can upload files (PDF, DOC, JPEG) to share with the administrator. These would only be accessible only when they login. Would administrators be able to upload files to this member's page directly?
That can be done with CB Gallery and yes CB Moderators can upload to users profiles.
4. Can the CB system allow a member to make an adhoc payment to access additional content to the site? eg, if a Level 1 member buys a "super" pass, will the system be able to reflect the "super" status?
Yes, this would just be a subscription in CBSubs that gives them access to whatever content you're wanting. If it's a one-off purchase instead of timed you'd use a lifetime subscription.