If we are describing investigating or searching something very specifically that was described in the scene, than no roll will be needed (ie. I check under the rug and automatically find the secret door if there is one). In addition, even if we are more vague (I check the room for secrets), but not hurried (ie. no negative to failing a roll), then we can use our passive values to find things automatically. Rolls tend to only occur when we can't do things repeatedly or there is a direct drawback if we fail.Does your DM ask for an ability check for just about any described act of investigating, perceiving, or searching? Or are there cases where you automatically succeed (or fail) based on how you approach something?
It depends on if we are in a group or split up. If in a group, then it is a group check. We have two stealthy individuals (wizard is +7 for stealth, ranger is +9, cleric is +0 disadvantage, fighter is +2 disadvantage). If we have pass without trace up, then we can do decently quite often. However, when we have a scout very far forward, it tends to be waves of stealth checks, first the forward ranger as individual and then the rear guard as a group without the ranger (which fails a lot). I'm not sure that is actually the correct call with all of the mechanics in play -- particularly if we are going to use the Help action to negate the dim light penalty for the ranger scouting.Is the DM calling for individual checks or a group check? In a group check, only half the group is required to succeed. This helps mitigate the chance of failure when you're skulking about with heavily-armored characters. The fictional requirement is that you're trying to accomplish something as a group (sneak around or get the jump on some monsters, say) and that the skilled characters can reasonably help cover the less skilled ones.
With that said, the ranger player really wants to scout since that is what he is supposed to do according to the stereotype. It seems kinda flawed if the system really wants to discourage that due to various mechanics.
Really, there aren't a lot of traps. Mostly it has been alerted people in ambushes and the occasional alarm spell and rarely something worse.I don't recall how the traps are telegraphed in HotDQ, but I'll take your word for it. Most DMs in my experience fail in this respect - and many of the adventure designers, too.