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I mean... He's not wrong. You shouldn't need your phone number or email as a requirement to drop off a prepaid package with a mailer. The courier service has that info there's no reason Walgreens should need it.

If you're getting insurance, asking historical insurance questions should give them a better understanding of your history, like if you're a brand new driver or not, etc. But it should not be required. Instead of "we have to know this" it should be "we need your history to determine policy risk and provide coverage. The less information we have the higher risk we have to assume and the more you pay. If you don't want to tell me your history that's fine, but you're going to pay more". In reality the insurance companies use giant databases to know exactly who and how you were insured. Payment histories, claims, everything. So it's moot and still wrong.

The sov cit movement is ridiculous, but they're not always 100% wrong in their stances.

Anecdotally I had a UPS Store try to pull the "you have to wait in line to drop off a package so we can get your details" crap for a prepaid drop-off. They can make you wait in line if they demand because they can ask you what's inside to determine if it's hazardous. That's their loophole for preventing drop offs. But they cannot demand your information. I'm not super important but do a fair amount of business with UPS for a rando (thousands $'s week which is a rounding error to them) and after a complaint, got a followup, and magically now they accept packages without requiring information. But you still have to wait in line for them there. The purpose of the information was to get you on the store's email list for promotions and presumably data sales.