Loudhy:
Some words about my early playing style. I'm playing expert ironman nowadays, so your plan could be possible. However, if its your first game in expert difficulty, don't be afraid to reload.
To your planed party: In expert without reload, they will be toast in Trynton (from Sprites), or in swamp/martens bluff (from monsters with ranged attacks). IMO in expert without reloading, you need missile shield, and you want to have elemental shield.
My start: Since i'm playing ironman, i want to be level 2 before i fight the noxious slimes, so i often have to search some monsters. Then it's easy to get for the king crab. Then with weak parties, i again scum for monsters to be level 4 against Gregor (visit Burz via the elevator before this fights, for healing stuff).
Somewhere in the monastary i reach level 5. Sometimes i have the experience to go to 6 before leaving, but i don't level at this point. IMO the first part of the arnika road is the most dangerous point. Once i reach the area with the house, i take my level 6, and level normally after this.
I proceed to arnika, doing all the stuff. Then to Mt.Gigas, for the flag and some books. And then the normal road to trynton. I'm usually level 10 when i'm finished with trynton; with small parties, i scum some monsters to be level 11 when entering the swamp, to be able to go straight to Crock for books.
Sultan - in my experience, it is easy to drag the crusher crabs around at the monastary entry, and then run around them to reach the road without fight. It's only bad if there is another dangerous encounter before the thieves hideout.
To little_yamir: the demon sting bow does double damage against demons. AFAIK he doesn't affect criticals; you could have got these kills with any other bow as well.
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