Safety is paramount. Always keep gear out of the spinny bits like your rear wheel and chain. Even something as small as a loose t-shirt that gets caught in your chain or wrapped up in your hub can bring you to a catastrophic halt. We’ve seen it all and most of the incidents were completely avoidable if the rider packed properly in the first place and checked their gear at every stop.
PRIORITIZE EASY ACCESS If the stuff you need to get at all the time is buried under the gear you don’t need until you get to camp, you’ve got it backward. Make things like glasses, tools, sunscreen, multi-tools, and extra layers easy to reach so you aren’t at a yard sale at every gas stop trying to find that chapstick.
Keeping an eye on your buddy’s gear while you are riding is a great idea – they most likely can’t see that bag mounted all sloppy on their sissy bar, but you can! The best way to avoid a dangerous situation is to pack a reasonable amount of gear in the first place. You are just going to Baja for the weekend, not moving there.