Interesting combinations there, Jack. With a little care, you should do all right in HOF mode with this bunch.
Suggestion: send your thief out alone (stealth mode) and get into Tamewater's house (no need to chat first). Grab the xbow. Head on to the Salty Dog. Buy the greataxe and bow from Guthwulfe. Also as much ammo as possible, but leave a couple of slots open for the other bow and spear outside the tavern.
That gives you three ranged weapons, one decent melee (axe), and one that's slightly better than the toothpicks you start with
If everyone beats on the same gobbie, that, along with the summons, should take them down fairly quickly.
I know this from experience
Nightowl2