Stripe Would Be Perfect If...

I'd also agree that dealing with taxes on Stripe is much more complex than it should be. It could be that there is no way to simulate time. It would be nice to see how Stripe reacts after one month subscriptions, or at least a few days, to get a real sense of how pro-rated prices are calculated in practice. I'd also like to see a better way to test webhooks in two cases: 1. when they are not successful and 2. be able to test webhooks with your application specific parameters.

You can make invoices by using their webhooks (https://stripe.com/docs/webhooks). Just email your customers when a billing event occurs

I'm sympathetic to Liam's grief with calculating taxes, and handling the edge cases of people moving around different tax zones. It's not exclusive to Canada, of course.

However, my perspective is that Stripe sits one level lower on the infrastructure map than a service like Recurly (http://recurly.com) which is designed to abstract the pain of subscription management away from app developers. I use Stripe first and foremost as a best-in-class one-time payment processor. There's nothing stopping me from building a subscription management solution on top of Stripe; I'd just be re-inventing the wheel.

Stripe's subscriptions strike me as a good compromise between nothing at all and something that becomes more sophisticated over time. If they try to stamp out all of those edge cases, they will inevitably break someone else's application that relies on a slightly different interpretation of "the way things are supposed to be".

I sincerely hope that Stripe continues to say No to feature requests far into the future. Where does PDF invoice generation (with HTML templates of course) fit into "the simplest thing that works"? When Stripe notifies you of a sale, generate your own invoice. Maybe even consider open-sourcing that code. Adding it to Stripe is not the best thing to do.

If they support coupons, I don't see why they can't support taxes. Taxes are just the opposite of coupons and should be relatively easy for them to implement.

It seems to me that creating several dozen subscription plans on Stripe is indicative of a deeper problem: that you have several dozen different prices consumers end up paying. How about instead you advertise the prices that consumers will actually have to pay? Bump up all of your prices across the board by the expected cost of taxes to even out the cost.

(Unless there's some law about not charging consumers in different provinces a different pre-tax cost, or some province charges so much tax that to make other provinces eat a share of that cost would be unreasonable.)