You're forgetting that mail order wasn't the norm--even if you ordered from a catalog you picked it up in person at the store. So, not collecting tax on mail order wasn't a big deal until Amazon flattened bookstores with it.
Per FRED[1], monthly mail order sales doubled from 1992 to the end of 96.
Obviously it was nothing like today, but mail order was, like, a thing.
[1]: https://fred.stlouisfed.org/series/MRTSSM4541USS
*Also, I learned in my google rabbit hole about this that it’s a 1992 Supreme Court decision that confirmed that mail order retailers didn’t have to collect state tax unless they had a physical presence in the state.
Note that we are talking about small rural towns in the middle of nowhere. When sears started most of the population was either a farmer, or lived in a small town in farm country. If you lived in a large city you could go to a department store downtown and it would have everything. If you lived in a small town the department store had only the very popular items and you were expected to order from them.
By the 1980s the population had shifted to bigger cities, and UPS offered affordable shipping to your door, so those small town stores had little reason to exist and started closing.
I get that it feels neat and tidy to say that Amazon and Uber had the same growth model of skirting regulations, but the facts don't match that.
This doesn't mean that Amazon is good--I think that what the effect of what they've done to retail is awful. But using Uber as the key piece of a kind of Godwin's Law doesn't really help matters.