The conversation between block and Jack seemed awkward regarding patreon/hivetips. Jack tried to raise a real issue regarding legality but block didn't really let him explain thoroughly and then dismissed it as "we don't need to worry were decentralised" which is false. As long as money is involved legality is always an issue.

I don't feel like he dismissed the issue. The legal issues come from the fact that middlemen like Patreon can fail to cancel (or setup) a payment or may take an incorrect amount.

With a decentrlized recurring payment those are none issues since the transactions are peer to peer. There would be no middle man responsible to make the transfers. The only way that a legal problem happens is if two parties setup a contract and one of them fails to fulfill his/her commitment. In that case the issue is only between the involved parties.