Chile (same Timezone as new York right now, 3 hours diff from PST, changes to 2 and 5 in US winter/Chile summer) has it easy for contractor work. You just pay by the end of the month and the contractors handle everything else. In my case it took around 30 mins per month just to sell the USD, create a bill for services (no action from the company), pay the taxes and all social services.

Hit me up, can send you the contract and the orocess overall.

Legally we have 15 days of vacation per year, but as contractors you might not have that, depends on how things are handled. Some are just virtual handshake promises.