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I assume you will be crossing at Lukeville. You need to be able to show proof of ownership at the border for the tow vehicle, trailer, and boat if you get the red light and are asked. Current registration slips are fine.
Mexican liability insurance on the vehicle and trailer is a don't go without it item but no one will ask for proof of it. But if you get into an accident without it you're in a world of hurt. But you already know this since you have gone down before.
You are supposed to have on water liability for the boat but I don't know of many that bother with it for weekend trips. The people that launch you will not ask for it. It is not like San Carlos in that respect. I reccomend using Safe Marina for launching services but you have other options that are cheaper. Safe Marina would probably charge you $25 for your San Juan. That includes launch and retrieval. Motor flush and boat/trailer rinse is an extra $5. I've been using them for years.
Going to RP via the Lukeville crossing is pretty straight forward once you cross the border.
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