While playing Fallout 3, at the time I thought lockpicking by rotating the pick was too easy.

Now, playing Oblivion, I see why they went to that way of doing it. Lockpicking in Oblivion is apparently random, and as difficult as it can possibly be.

There doesn't seem to be any timing between pushing up a tumbler and jerking the lock. If there is any timing, it is literally within a 0.050 second to 0.200 second window when the tumbler is jerking upward. I'm sorry but I don't have instantaneous reflexes.

I haven't found anyone who teaches lockpicking yet though I did find the thieves in general.

I believe I have blown through some 400 lockpicks currently at level 11 or so, and I'm at about skill 34 lockpicking. Since only the first 100 or so were from containers, that's 300 * 5 gold simply thrown away on failed picks.

It appears the only skillup occurs when the tumbler goes up and locks in place, but not really from actually opening the lock itself. So to skillup you apparently need to just take a deep breath, get about 200 reserve picks, park yourself in front of a Very Hard lock, and just keep picking away, not necessarily intending to open the lock but to just hope for the occasional locking tumbler and skillup event.

I'd say lockpicking is most random and difficult in Morrowind. Unlike F3, OB, or SR, there isn't a minigame for picking. You just use the lockpick on the locked object and hope the RNG is nice to you. Once you get the skeleton key (which in OB is really easy) lockpicking becomes a joke.