Good news!
There is now a Site Setting for automatic tax collecting discourse_subscriptions_enable_automatic_tax that you can enable. So that you can collect tax without having to use Stripe Checkout.
https://github.com/discourse/discourse-subscriptions/pull/218
If you enable it, but you have not configured your stripe instance properly to collect tax users may see this popup after completing the checkout process:
There is this guide for more info, but there shouldn’t be much do since the plugin is now passing in the appropriate automatic_tax[enabled]=true parameter (step 5).
Be sure you configure your registrations (step 4) as well:

