I've always gravitated towards rogues and skillmonkeys. And I have many complaints with 5e, but on the whole I find it fits my style of play: I like to play someone competent, but not in a "I can do anything!" sense, or "I'm super mighty and deal a million damage per turn". In a grounded way, more like a specialist. These are my strengths, these are my weaknesses, now how do I solve problems by taking advantage of the former while compensating for the latter.
In AD&D 2e (my starting point), I couldn't play a competent thief. The rules wouldn't let me. The rules told me that I have, for example, a 30% chance to successfully pick pockets, in any and all contexts, and there's nothing I can do to stack the deck in my favour. I was thinking, what if I tried to take advantage of this street spectacle that's distracting a big crowd? What if I tried to choose a victim with a poorly secured purse? Nope, nothing mattered, it was still a 30% chance.
In D&D 3.5, I could play a competent thief, but I had to make it happen in character creation and shopping sessions. Basically for anything that wasn't a full caster, to achieve competence I had to take this race, that subrace, the other template, these 4 feats (need a flaw to fit them all), dip this class, take that prestige class, and more importantly stock up on magic and mundane items to boost my check with all these different modifiers. [Note that when full casters did that same process, the game fully broke.] Number Go Up is the name of the game. And then, if I did something clever in-character, the DM might deign to grant me a +2 circumstance bonus.
In D&D 5e, whose skill system leaves so much to be desired (esp. 5.5, which kind of abandoned all rules and guidelines about it and I'm still livid), I actually can play a competent thief. I don't need to change my character concept and choose a whole other species just to get a Dex boost that thieves can't do without. I don't need to look like a christmas tree full of shiny magic items to do what my archetype is supposed to be doing. Rogues are good with skills and you can select which you're good at, Thief Rogues can pickpocket extra fast, and bounded accuracy keeps Number from Going arbitrarily Up. And then, when I do something clever in-character, the DM grants me advantage, which meaningfully affects my chances to succeed.
Downside: the DM has no idea how to resolve pick-pocketing (i.e. what the DC is), unless the DM is already versed in these things from previous editions, D&D variants, or homebrew. Otherwise, all they got to work with is a vague DC range from trivially easy 5 to nigh impossible 30, and "some checks are contested".
Upside: The DM can quickly learn what works best for theirs and the group's preferences, and adapt accordingly without breaking the game, and also I don't play with newbie DMs, so I don't care.
So that example was probably too specific (in many campaigns pickpocketing never comes up), but the broad point stands. In 5e I can portray selective competence (my favourite!) without taking 4 days to build a character. So I'm good with it.