I think cashless, in the sense of "all money is digital", is probably a net bad thing. Remember, there are governments and organizations today that don't believe in basic freedoms: one could, for example, know if someone gets an abortion by looking at their payments history. The privacy cash provides is important for society as a whole.
On the other hand, I think a lot of this "cashless" debate can be fixed by mandating any merchant of goods or services to accept cash. Parking meters, brick-and-mortar stores, etc. have all been accepting cash for a long time, so it's a solved problem.
The thing about the "I need cash in order to do things the government doesn't want me doing" is that it's just incredibly precarious. Very difficult to use that as an argument to government or its supporters. And it tends to "evaporate" over time as people stop using cash for "legitimate" purposes. So you end up with nonsense like US asset forfeiture, where the police can simply steal your cash.
> mandating any merchant of goods or services to accept cash
The fewer people actually use this option, the more likely the merchant is to be very passive-agressive about refusing it. Like claiming not to have change.
On the other hand, I think a lot of this "cashless" debate can be fixed by mandating any merchant of goods or services to accept cash. Parking meters, brick-and-mortar stores, etc. have all been accepting cash for a long time, so it's a solved problem.