I think the difficulty of the first town is about right. Players who have built a crappy character (eg, 10 strg, 10 dex, 4con...and everything into the merchant skill, cuz I'm a merchant!) should see early on that their character sucks my balls and needs to be redone. It's not like they have to get halfway through the game for it.
People don't like redoing their character. It's like saying their choices were wrong, and in that case where's the freedom???
So any choice no matter how retarded should be equally viable? What if you play a fighter but put a single point into a weapon skill? Should we honor that too? After all, it's your choice!
I'd suggest hints in the chargen screen telling you what skills a class would be expected to have, and such.
Jesus Fucking Christ.
Do you need to be told that a merchant should have trading, persuasion, streetwise, and etiquette? Cause these are the main skills. Or that assassin should be good at killing targets fast (CS)? Or that a thief who wants to be a highwayman should be good at fighting and a thief who wants to be minimize combat should have disguise, stealing, sneaking, talking his way out of trouble, and such? It's not exactly rocket science.
The whole meta-gaming thing only become an issue when you want to get more content, content that lies outside of your character's domain. Then you need to know that putting a point here and a point there will unlock something extra for you.