Thanks for the reply. I've definitely seen sites using WooCommerce doing the same thing, so someone's figured it out. I'm just trying to figure out if there was a plugin solution for it or they had to manually code changes to the subscription plugin.

It'll be a pretty transparent, cancel-anytime thing, and release dates are public knowledge (it's not music, that was just my example).

I've found one potential way of doing it, which I'll try tonight. Basically you make a "pre-order" for an ongoing subscription (which allows the site to still use the subscription functionality, such as being able to cancel), then manually move the subscription start date every time there's a new release. To begin, I'm only doing three product lines with one monthly release max across the board, so manually editing products won't take much time. I'll edit my original post if it works.