Were you the one who was sleeping in that car in the video from the OP:OP2 AAR? :P
In terms of most airsoft games, with their relatively short durations of 24 hours or less, there doesn't really need to be a hard-and-fast rule about when to sleep, and when not to. You should take your chance to sleep when you can, and just get used to going in and out of sleep. Most of your chances to sleep will likely be dependent on your squad, and on your team's commander.
If command sends your squad out to defend a location, then your squad leader should work out if he can spare people to take a nap. He should be checking in on everyone to see how they're doing, and if anyone needs rest. When you feel tired, you should take the chance to sleep. If you're going to be posted up for a while and the squad leader asks for volunteers for the first sleep shift, you should take it.
If action happens later, you'll be woken up. If you don't take your chance to sleep, and action happens later, you won't get a chance to sleep.
Make sure you don't let yourself fall into a deep sleep, though. Your squad should be waking up the sleepers every 30 minutes (give them about 10 minutes to pass out, then let them sleep for 20) and forcing them to move around, and eat/drink something. Once you hit REM after a hard day's fighting, it'll be hard to drag you out of it.
Really, it's just willpower to keep yourself from crashing. You grab your rest, and force yourself to wake up. It helps if you've got a squad that knows you, and can push you.
If you find it as hard to wake up as I do, and a "sense of responsibility to your squad, and to your team" is not enough (it's just a game, after all), then you certainly shouldn't be sleeping in a tent. Sleep in a building, or on the field. Ideally in a place that once you wake up, you can roll over and stand up in. You need to force yourself to move once you're awake, or you'll fall right back asleep. And, like entering a cold lake, you have to just suck it up and jump right into things. If you're laying in a tent, looking at the door that you have to force yourself to crawl out of, into the cold dark night of milsim shit, it'll suck some morale out of you. If you're just laying in the field, and can roll over, grab your gun, and stand up to talk to your buddy and ask what's been happening, it's quite a bit easier to get up.
So bottom line: rest when you can, and just use will power to get yourself awake before you fall into a deep sleep. Your squad leader should be on top of things, and should be dictating when you sleep. You just need to provide him with appropriate feedback of your status. Lastly, your squad should help to limit the length of your sleep in a single stretch of time, and be able to push you to get up. You're part of a team, so your teammates should be able to do this for you.
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