having the guilds polarised is a good idea. by having them being enemies of one another; warrior vs mage, religious vs merchant (this can be a big twist, i'll elaborate later), thieves vs cult, etc; one can expect all sorts of outcomes though the main outcome of the game would be inevitable; your two endings.
like lews said it, kiya, it's your show so we'll concentrate on your dream. <img src="/ubbthreads/images/graemlins/winkwink.gif" alt="" />
now, about morbo's idea of learning that higher or even 'ultimate' level of certain skill(s), one must go to certain teacher(s) who has long 'resigned' from any position in the guild. & that old geezer(s) will be very pissed when he/she learnt that the current guildmaster just sent somebody unknown, untrustworthy (at least to that old timer), & unwanted to him when all he/she wanted is to go fishing or organise frog races with other old timers in his area. so what is he/she going to do about our hero(s)?
old timer can send them on 'quests' so that he/she can be left alone to do his/her usual daily activities. get rid of the pesky hero-wannabees, the old timer would say. his/her friends around him/her would whisper or even shout to him suggestions to get rid, er..., they mean to send the heroes on 'important' quests. if the heroes found themselves fooled by the oldies & want to do something about it, they will need to have high enough skills in diplomacy to convince or nag the old timer enough to teach just to get the heroes off his/her back. if the heroes however impressed the old timer enough with the mundane quests (requirement: total success in quests with impeccable result), he/she may throw in a freebie or two.
thing is; no promises for the heroes. so heroes have to decide if the old timer is playing around just to pass his/her time & have a good joke to tell his/her friends or is that old geezer serious. again, diplomacy/charisma skills matter here to open up more dialogue trees.
as for weapon skills, i wonder if it should be bestiary knowledge skill? ok, let me explain;
instead of having different skills for different weapon or damage, why not learning how to kill particular beasts & monsters? by learning that, one can harness his/her killing skills to put the enemy down. this can be learnt from teachers or by experience. experience would be that if the player kills enough of the same enemy, he/she will be more efficient in killing them. in proportion to that, players receive less XP points in killing them. if one learns it early from a teacher, then one will receive a chunk of XP points followed by trickles of it when actually killing the enemy.
2 more cents have been added. <img src="/ubbthreads/images/graemlins/smile.gif" alt="" />