Need Advice - Customer Digital Uploads: Single Order and Subscription

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I'm looking for ecommerce software that accommodates the following functions.

Single Purchase:

Customers choose a price package for what level of services they want. They then upload individual files (as many as they want), and the rate for the chosen package is applied for each file uploaded. For example, the customer chooses a package that includes basic features, which is set at $5 per upload. The customer then uploads 10 items (or as many as they need) to be processed. The total bill is $50 in this case.

I can't seem to find a service that will let me bill per each customer upload. The closest I've seen (that looks clean and functions well) is WooCommerce Upload My File, but here it looks like I have to set a product price and then the customer can upload as many files as I allow, but it does not bill the customer per upload.

Subscription Purchase:

Users purchase a subscription option, where they pay x-amount per annual subscription and can then upload up to 100 items to be processed. In other words, customers would purchase the subscription for a term (1 year) but their number of allotted uploads would be capped at a set number during that term, or until the subscription was renewed. Kind of like a movie subscription where you can only download up to 20 movies per term, then you reach a limit and have to renew the subscription, buy a better package that allows more downloads, or wait until the next pay cycle. Only with my store, it's for user uploads.

Any suggestions for software that provides these functions is greatly appreciated.

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