Hi,
It sure is possible to do exactly like you want. That will require the development of a custom plugin to handle all that and probably some view overrides to add the new interfaces needed for that.
Jerome was only pointing to the fact that HikaSubscriptions has a subscription system which might be usable to help a bit reduce the development needed.
In any case, that will require a developer to work on that for you.
If you want us to work on that for you, you can contact us here to go deeper in details on what's required with us:
www.hikashop.com/support/contact-us.html
It would be great if you could do screenshots of the interfaces where you see new elements you would like. For example, the orders are displayed on the user control panel and on the orders listing on the frontend. If you don't have menu items leading to these pages (and the customer only access his orders via the link on the email notifications), then there is no point in modify these interfaces for your needs, only the order details page would be concerned. Knowing what you want where will allow us to give you a quote on the development.