Usage subscription

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Hi all. I'm developing an on demand laundry service website. I've got most of the issues sorted out except one.

For example I'm launching an offer, where I have a monthly subscription model.

The offer is-  get monthly 3 times free doorstep laundry pick up and delivery of total 100 pieces of clothes for 50$. 

basically when someone purchases this offer, they can schedule free laundry service 3 times in a month for total of 100 pieces. So for example they can send in 30 pieces the first time, may be 50 pieces the second time and finally 20 pieces.

My question is how can I keep track of a customer on how many times we've offered pickup and delivery and mainly how many pieces of clothes I've laundered and how many are pending. 

I want it to work in the following way.

When customer places an order, a msg and mail is sent for confirmation. 

Next for example the first time we pick up 30 pieces of clothes, launder them and deliver it to the customer. When this is done, I want the customer to get a notification through mail stating that they have consumed 30 pieces of clothes with 1 free pickup and delivery and they have 70 pieces pending with 2 free pickup and delivery within a certain date based on the date they ordered. 

Also I need to have the total usage details of each customer so there's no confusion. 

I want it to be automated and don't want to physically do the book keeping of each customer. 

I hope I've explained myself clearly and looking forward in some great solution.