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Guards will only let you keep one lockpick, if you had one, even if you had 1000 of them. It is counted as something you managed to hide and take in with you.
Some skyrim jails can be broken out of ... others you could break into to plant gear to use, to break out.
This post sparked conversation and few questions about these mods and methods in the chat, so I figured it would be better to type them out for all, instead of replying to just one through a very small window.
Guards will catch you eventually and bribery system is somewhat strange. I am using this mod, so that running is an option. Now getting caught actually means that you got caught and had to surrender.
Crime Bounty Decay by cyberspyder
http://www.nexusmods.com/skyrim/mods/51247/?
Of course I am also using Death Alternative. If guards kill my character, then he/she does not actually die and reload the game. Character ends up in to prison instead. This means that I have to consider between surrendering and paying the fine (if possible) or trying to fight and risk serving a longer time in prison, which would hurt my skill progression.
These two mods make it so, that my character has a reason to sneak around, run when spotted and use mods like Campfire to stay out of the city and sneak in during nights, if he has to.
Solitude and Windhelm both have alternative routes in. Riften routes are directly guarded, but Argonian Access from Ruffled Feather gives a third way to sneak in to city, avoid vigilant guards and sneak out again once done. Markarth guards can be avoided with adequate stealth and getting creative, so this leaves only Whiterun as the only city without access, if guards are after you. They can all be distracted though, even without any mods.
If you guys are interested of playing thief characters, or just give your other character types a way to both avoid trouble and get in to it, then you may wish to take a look of mods I mentioned.
http://www.nexusmods.com/skyrim/mods/11158/?
Gives access from outside, which is great for werewolves / vampires or thieves!
The only thing is being very careful with how to install it. Follow those instructions to the letter.
Locks differ from Novice to Adept. All the other stuff is moved to a chest that usually has a Master level lock.