I'm a newcomer to p99 myself, but this questions seems to be a matter of personal preference for what you want to get out of the game. I think you will find joy in playing your monk/rogue regardless of being destitute to start off. As you level up, gear will come and if you choose to join a guild you shouldn't have a major problem obtaining upgrades you have your eyes on. See you in game.
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Spearfish/Symbiont/Detritivore/Roubaix
Accipiter/Borealis/Phelper
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