We have custom code that determines the VAT rate to charge, and also looks up a customer's VAT number to see if they qualify for VAT exclusion. At the end of each quarter I have a script that calculates the amount of VAT to be paid to each country in the EU, then visit the Ireland VAT OSS site, input the values for each country manually (they don't allow CSV!!!!), then send them a wire using wise.com.
The current scheme is an evolution of what the former founders did. It was a nightmare to get things onto good footing after the acquisition. But once I did it for the first time, the subsequent times are pretty straightforward, and I probably won't touch it again for a long while.
I could probably move towards stripe tax, or paddle/lemonsqueezy, but the migration would be a nightmare. And it's not a good business decision to do a lot of work including risky migrations to move onto a new provider that will charge a larger percentage as a service fee, just to better handle taxes, which I've now largely figured out.
The one advantage to doing all this, is that I actually understand this stuff pretty well now, rather than it being a black box where I just pay a company a lot of money so I don't have to think about it. Open question on if that's actually worth my time. It seems like it is for now.
One opinion I'll offer, is that all these foreign tax agencies are far less organized than you might think. You could probably get away by not paying VAT, for far longer/more revenue than you'd think, and if you do want to be a proper foreign business and pay, there's basically zero verification on if you're paying the right amount, so just try your best??
Feel free to ask me for any advice around VAT/etc. matthew@improvmx.com