Charging Licenses for Online Courses with LearnDash

I would like to restrict access to courses, pdfs, ebook, videos, etc. across a site and charge for access. Some products would be a simple subscription model for access but courses (managed by LearnDash) would be a per license model.

We would need to allow a customer to buy 50 licences to a course and then distribute those to their participants of a program.

We sell training courses to plug into mentoring, coaching or leadership programs, therefore often our customers want to use our training for their participants. We want to charge licences to use the course per annum per user whilst allowing the program manager to allocate the licences to their participants.
Could we package this up with subscriptions as well? For example could we charge an annual subscription to a package which included 50 licences to our course plus annual subscriptions to other pages located outside Learndash that included pdfs, ebooks, videos and other software.

For example customer Joe who subscribed for access to 50 'X' course licenses at $… per annum has access to product 'X' through his page permissions but he doesn't have access to product 'Y' pdfs or 'Z' ebooks.
Customer Carly subscribed for access to product 'Y' at $… per annum and 'Z' at $… per annum so has access to product 'Y' and 'Z' but does not have 'X' course licenses.
Customer Bob bought the package deal and has access to all product pages with 50 licenses of 'X' course.

I'm assuming for this kind of functionality we would need to do some customisation to have all of the plugins synchronise in this fashion but I would love to hear your insights into how and if it can be done. Look forward to your response.