getting the key from pickpocketing doesn't sound too good for me. after all you're in and the guard is out the cell. having him walk close a cell door while the prisoner is just by, and actually get pickpocketed would really make him deserving of a cruel death
a pickpocket action would have to occur when the guard was in the cell or close proximity to the prisoner and bars.
perhaps two prisoners arrange a distraction that brings a guard within pickpocket distance of the bars. this kind of stuff is done in movies and tv all the time.
two great reference movies who's inspiration i see in this tread's ideas are "the great escape" starring steve McQueen, and "escape from alcatraz" starring clint eastwood.
think in terms of techniques, not technology, and it should translate well to a medieval setting.
also look to Zorro, The Cisco Kid, and Errol Flynn movies for creative ways to escape things.
almost everything mentioned here i can recall having seen in some movie or tv show as some point.
4. it's not really ruled out, I just don't want a really obvious and unrealistic access to lockpick materials, which is why cells are pretty much empty. I know grinding rocks to create a lockpick sounds too forced/unrealistic, but that's the best I could come up with at first. what about using a rock to grind a rat/meal bone to create a lockpick?
ever tried to pick a medieval cast iron lock with a chicken bone? <g>. probably not happening. in the real world, you'd get some metal (somehow), then spend days/weeks/months grinding your key or pick.
indeed these may be combined together, but since I want different options and there's only so many reasonably ways you can escape a prison cell, I'd rather not waste options by making one out of two.
what you do is use those that can be combined to expand the list of options. so if you can escape by means A, or means B, or by means C followed by A, don't just give then C followed by A, give them both A, and C followed by A as options. combo = greater variety, not less. OTOH, these combos may not exist. in the example above, why do C then A if you can just do A?
so you'd need escape by means A, or means B, or means C followed by D kind of thing. whether any C followed by D kind of things exist? thats another question. if so fine, implement them if it makes sense,. if not, that's life, there are only so many options, and you just live with it. if it turns out the options are too few, you probably don't have sufficient mass as far as "topic" and limitations goes (escaping from prison cell) to make an interesting game, and you'll want to figure out what's lacking. this can happen. its happened to me. turned out ok, added another dimension of gameplay, and it turned into my biggest hit ever (free tv press on the evening news prime time in the nations capital ! )