I think a proper system for "degrees of success" is needed here as well, especially for characters with Expertise options like the Rogue. Too often, skill checks are "you roll high, things proceed without incident/you roll low, bad things happen".
It was funny, just earlier tonight, I went downstairs and my roommate was watching Critical Role. I don't watch the show, but he paused and was like, "hey, let me show you something".
For years now, whenever we play together, and we take watches for the night, I've noticed this trend. The DM asks you to roll Perception. If you roll high, nothing happens. If you roll low, there's an encounter of some kind (it's a rare day when you roll high and can react to enemies by noticing them first).
So he's showing me this bit where the various characters are roleplaying out their watches, and Matt Mercer is like "roll Perception checks". Two characters roll a 17 and Matt says "It's very cold outside". My roommate said he laughed when he saw that, because he immediately was reminded of my usual gripe.
(Although he then went on to say that in a previous session, someone rolled a 1 on their Perception check and there wasn't an encounter either, so no indictment against Mr. Mercer, it was just an amusing moment.)
At some point, after noticing this trend, I started making sure my characters were good at Perception, and my roommate followed suit (eventually followed by the rest of our playgroup). We haven't had a nighttime encounter since.