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this was long and a bit rambling, but lots of food for thought. the Internet Archive has a sort of "slow support" approach where it takes a while to respond, but are then pretty responsive. you can call on the phone and talk to a person!

I was pretty impressed with the Stripe support culture when I worked there (several years ago). they had engineers train and participate in support during on-boarding, support requests tended to take priority, etc. this was all "merchant support" of course (Stripe is B2B), not end-users