Woo Commerce Custom Field Integration

So we're working with WooCommerce and we would like to switch our E-mail service to CM. I'm not finding any simple solutions or current integrations for my problem, and I'm hoping for some feedback on how to tackle it.

I want to have everything on one list and then sub divided in to segments based on Custom Fields. We Have 10 Products, 3 Free Products, Mailing List, Teaser Leads, Employees, and Press - so 17 Custom Fields:

Sense a user can come sign up for our "Mailing List" option, come back later and sign up for 1 free product, then may later come and purchase 3 items, I need to have each of those reported in a Custom Field, so I'd like to have each custom field only populate when they purchase a specific product or get a certain free product.

For Example:
Custom Field "Product1" will only populate with [Name of product] when Product 1 is purchased.
Custom Field "Product7" will only populate with [Name of product] when Product 7 is purchased.
Custom Field "Mailing List" will only populate with [YES] when the user signs up on our Mailing list web form.
Custom Field "Free Content 2" will only populate with [Name of Content] when Free Content 2 is sign up for on a web form.

This will prevent any thing from being over written, and it will make it easy to segment out many combinations of customers owning a variety of products.

Also, I'd like these to integrate with Transactional e-mails. So when they purchase a product, they get the invoice, account creation e-mail, etc. and become part of an automation workflow.
When they sign up for "Free Content 3" they get the download e-mail and are added to an Automation Workflow.

Is there an easy way to set this up that I'm missing? Or is this going to take a lot of extra development? Or is this not at all possible?

Thank you in advance!

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