It's been a long time for Stripe to introduce a solution for taxes after it was requested by lots of customers (and recently acquired TaxJar because of it)
The US just has a convoluted tax system.
I wouldn't go as far as to say they've fallen to the "bean counters" but they definitely aren't as customer obsessed as they have been in the past and quite a few gaps in their armor are becoming obvious.
But it does sound like we did drop the ball with you, and I'd like to figure out what happened if you could forward me an example at edwin@stripe.com.
They are arguably best in the industry doesn't mean they are as good as they once were. Apple Retail experience, App Store curation. Butterfly Keyboard? If if it trend we are talking about then Apple is no different to other company you mentioned.