Money near Freeport is rough. Best bet is Bone Chip stacks (though he'll need to keep some obv). Also, kill Bears and hope for HQ skins. Every char I lvl in any area with Black Bears usually gets at least one. HQ Cat and Wolf skins can sell but not as often and not for as much.
As for strategy, until about 10 you guys just run up to stuff and smack it down w/ pet in tow. Once he gets his "mana for hp" type spells you can keep him topped off and he can keep it up 100% of the time. Once mana pools grow enough and such, fear kiting will be king. Don't underestimate cleric nukes, especially vs undead. Go to Unrest as soon as you can. One of you should be able to lull (or lull undead) and kill beetles and the like. Otherwise, just get croc groups in oasis. It's tedious but he'll get to practice his mojo in the safety of a group. As a cleric, you'll get in any group there is and can use the magical phrase "I'll only join if my friend can too."
If you have any more specific questions feel free to PM me. I'm an alt-o-holic and I'm pretty sure I've leveled in almost every place you can.
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[60 Oracle] Psilocybin (Bear) <Taken>
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