first boss
I finally got past the first boss!
what I did was this:
when you make your character, give him a high charisma bonus
at the very beginning by the lousy dagger, as you can enchant it for free. the only armor you should buy are the cheapest boots.
then get all of your duels over with, without any losses. and the minute you get the crowd thingy use it as often as you can, because it will earn you more money. this process should earn somewhere around 4,000 gold.
use this opporatunity to get all of the best armor that you've been waiting for. Now enter the turnament.
again, use the crowd pleaser as often as possible in all of your matches.
Now comes the boss. in this fight, forget about the crowd, taunts and rest. just get close enough to hit him with a charge attack, then continue to hit him with quick attacks with the hope of freezing him alot.
i can't garruntee this will work, but it was how i beat him. and the prize money is well worth it.