A plugin to keep track of each member's progress

Usage idea 1:
-a club where everyone owes $10/year.
-member 4 paid and now owes $0.
-next year comes around and member 4 now owes $11 (dues went up).
-member 7 hasn't paid and now owes $21.
-member 7 pays $21 and now owes $0.

* Have a link to PayPal with the amount.
* Have an option for increasing the fee so the recipient doesn't get charged the PayPal fees. For example, member 4 owes $10 but if they choose to pay via PayPal, it'll go through to PayPal as $10 + $10 x 2.9% + $0.30 = $10.61 (note: NOT $10.59, since we have to NET $10).
* If they choose to mail in a check or pay cash or whatever, ability for Admin to mark "paid via check #1234 on DATE".
* Ability to add late fee/percent after x-days overdue.
* Ability for each member to see their charge history and payment history.

Usage idea 2:
-new order comes in. Progress = 0%.
-step 1 is to order the documentation. Once docs are ordered, Progress = 3%.
-step 2 is to get signatures. Once done, Progress = 7%
-step 3 is to mail off the pages that got signed. Progress = 15%.
-etc.

* The company/employees can update the progress and make comments (i.e. workflow).
* The clients can login and see their progress, target completion date, items needed from them before proceeding, etc.
* Could incorporate upload documents form (compatible with SSL) and some other features.

It could be very simple or complex.

Do you guys have anything like this now or anything in the works already? If not, I'd like to request it.

Thank you.