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Very nice write-up. We had the same requirements and went through the same stages and similar conclusions. Though we opted for #2, using Stripe+Quaderno, to create us tax reports. The VAT submission and processing by our accountants has been trouble-less. A bit extra paper work (well, PDFs) but the accountants do most of that. Quaderno writes and emails the invoices and there's some issues with customization, never mind some users get confused seeing both Stripe and Quaderno URLs. Automated testing is a challange with two API involved, we found mocking responses to be impossible, and both APIs keep changing over the past years. Starting fresh in 2020 we might have gone with Merchant of Record, too.
Note that VIES is a government system that has been known to be down for maintenance
Way too often. And each country has different maintainance windows.
Post-Brexit, I guess that the UK will be treated as if it were a non-EU country
That's our assumption, too.
I think that it is generally a bad idea to rely too much on a single provider. What I want from a payment processor is to handle payments, that's it: collect this money of money from that card and deposit it to my account.
This is more work so may not be your first step, but IMHO this should be your goal to be achieved sooner than later.
Tax handling is a big gaping hole
(Edwin from Stripe here.) I agree and we hear you—and we’re working on ways to fix this. If you’re interested, shoot an email to kmoriarty@stripe.com and me at edwin@stripe.com.