> If you are selling a vintage Gameboy DMG in pristine condition with the original Pokémon games that your dad bought you 30 years ago - I should be able to pay you $150 (or whatever price we both agree on) without anyone taking a chunk off that transaction, or even knowing it happened. Note that your father already paid his taxes for the transaction when he purchased the Gameboy, 30 years ago.

AFAIK in Canada, secondhand sales are still subjected to the sales tax, which is 13% in Ontario. I noticed this because thrift stores like Goodwill still charge the 13% HST, despite the fact that they're selling secondhand goods that other people have donated for free which have already had their HST paid on their initial purchase.

In fact, you re-donate the item over and over again, and each time a sales tax will have to be paid. The government is totally double-, triple-, and n-dipping on sales tax despite the fact that no new goods have been manufactured.

Another thing to notice is that this disadvantages used goods compared to new goods. If used goods didn't carry the sales tax, they would be cheaper, thus consumers would be more incentivized to save money and do the right thing from an environmental perspective. But because sales tax apply to both cases equally, there is a bigger incentive to buy the new goods.