IRL, learning to crack a lock comes down to patience and dexterity, right? There are classes in Skyrim, yes...and barbarians don’t start with a great lockpicking skill.

But the skills aren’t locked. So just like IRL, you can take your character and have her learn, for whatever reason. Maybe the barbarian is in a group of dungeon divers, and she notices the thief class they hired to pick all the locks always comes back from trips to town with better armor or a better weapon. And she watches the thief, and notices - he’s the first one to see the loot, and he keeps a little extra for himself each time.

She could beat the shit out of the thief for being a cheat. And she might - she’ll keep her options open. But also? She might decide to learn a new skill. Why can’t she be the first one to the loot chests? 

And it may seem like I’m making excuses to give my character aaaalll the skills, but sometimes people have hidden depths that make them more interesting, and cool stories behind why they developed those hidden depths in the first place. For example, I dated this soldier years ago. Really gruff guy. Big, tough, hands the size of dinner plates. Very much a “smash through problems” type of person. He invited me over to his place one night, wanted to cook me dinner. I’m not sure what I expected, but I was honestly astounded to fine out the guy was basically a gourmet cook. Unbelievable. And I remarked on it, that it wasn’t what I expected, because I was a lot less tactful back then, and he sort of shrugged and said as a soldier, he ate way too much shit food to accept it in his own home. So he learned. 

It’s not lockpicking, I know, but giving your character motivation to learn a new skill can make a roleplay that much more fun. 

It does, doesn’t it? I have a friend who plays D&D quite a bit, and she says when she gets to a point where she has to make a choice, or you know, there’s a chance of things happening to her or not, she can sort of hear the die rolling in her head. It sounds hilarious. 

Ah lockpicking, pull up a chair if you will.
For a year now, give or take, I have taken up lockpicking irl as a hobby.
It's actually my favorite hobby now besides gaming (and just as addictive to hear that click when a lock opens as lvl'ing up in game).
Spend over €100 (about 120 USD) on equipment and practice locks.

The thing is, it's near impossible to make a lockpicking system in game that can come near the real thing.
It's all the little feelings in both hands, vibrations and sounds that make it, well.. click.
ESO comes near(-ish) to what's actually happening inside a (modern) lock, anyway you can SEE what happens..
It's just.. no.. (I understand they have to make it accessible to any and all players, so in that regard it's fine.)

Locks nowadays work with pins, which can be normal or security pins. Though I am unaware how medieval time locks worked, I do know a few basics.
And even the same priniciple that works with modern day pins was often already a thing in medieval times, though in different shapes.
To pick a lock one must apply rotation tension to the lock, so that the pins will lock into place when pushed with the actual pick.
Applying tension has the biggest learning curve in lockpicking.
There are as many different tensioners as there are different picks (unlike the 1 shiv and the 1 pick that we see in skyrim.)

As to how many tensioners and picks one can realistically carry, well, I have 8 different picks and 9 tensioners in my every day carry kit.
While wearing a suit I can easily have 10 if not more of those kits on me without it showing I carry anything with me.
There are kits available that have 130+ different picks and duplicates, while not being larger than a handpurse.

So how do I rp lockpicking?
If I play a thief I can carry all the picks I find.
A warrior may carry a few (10-20) to try his/her luck, but I often resort to 'breaking' a lock or the chest. (I must say reading above there are interesting points that handle it far better than I have xD)
With mage I do have a mod that gives the 'open lock' spell, otherwise casting a few alteration spells as mentioned and console commanding it open works for me. (So no carry of lockpicks, unless the char has an interest in locks, like a hobby or just has to know all the knowledge ever.)

When I pick a lock in game, I only succeed if I manage to pick a rl lock within a certain amount of time.
For higher level locks I switch to rl locks with security pins, that are harder to pick. (Have those laying on my desk or near at all times).

So yeah.. a short introduction to my view on lockpicking ^^
Feel free to ask any questions.

Very cool, a real-life lock picker! I bet that click would be addicting.