Is he better? Just because his character sheet says he has better bonuses to do them doesn't mean the player is better. RP is not trivial and the character sheet elements it's based on are not the stats and bonuses on the front, they're the character traits, bonds, and backstory on the back.

That’s fine and all, but ultimately all of that stuff doesn’t confer any higher chance of success beyond an occasional use of Inspiration. I totally understand the argument you’re making (my only previous roleplaying experience was on a different platform that was much more freeform in this way), but it just doesn’t seem like this line of thinking is reflected in the mechanical realities of DnD, unless you have a DM that is very generous with giving out advantage.