There's definitely a disparity between the dungeon chests and the one's you nab after completing a Tmap..
I can't imagine the lockpicking XP being a "reward" though.. the chances of it going up are slim, especially once you hit 95.. It takes much longer.. The prisoner chests are usually the primary source of lockpick training after Haven.. at least to my knowledge..
As for BlaZe's script.. well, mine actually raised to about 95.9, but that was because I was afk for another hour or so past the point my skill hit 95.. So I'm assuming it might be possible to hit 100, but it'd probably take 2 days or so worth of afk macroing..
