I've done unconventional character classes for fun, and personal character traits only barely affect things. I always try to not abuse anything too much, but it just happens naturally sometimes when you decide you want that one class you never got before.
But yeah, what you're saying is really true of any video game, I'd say. It's also obvious with persistent online games like World of Warcraft. Every single new expansion, people would always bitch about how WoW is now "dumbed down" or "easy" when the game has only gotten harder every expansion, but they fail to realize the effect of playing the same game for years and years. That's not a dig at WoW as I always loved it, and I'd probably still like it if I played it now, but I recognize that average skill level goes up the more you play a game. To be fair, I can't personally know what the game's difficulty was really like after Mists of Pandaria, but I know what I'm talking about for each expansion since Classic through the end of MoP.
And in most games, the more you play a game, the more binary things seem, and then, indeed, the game pulling cheap things is the only way left to challenge you. It's sad, but that's why it feels like we always need new games instead of living on one or two forever no matter how much you love those couple of games. Look at how anti-fun the extremely hardcore Smash Bros. players are. They're sickening to me.
And don't get me started on the subjectivity of what even is true "skill" or "difficulty," ugh, lol. Safe to say those are nearly entirely personal reflections of your gaming experience/history.