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It's just natural that Cao Cao will have difficulties conquering the remaining Yuan Shao's territory even after Guan Du considering Yuan Shao himself has a hard time conquering Gongsun Zan who rules in that territory before him.
Cao Cao could for sure conquer the rest of Yuan Shao's territory if he go all out even when Yuan Shao is still alive, but you have to remember that during the moment, Cao Cao has enemies on all side(Liu Biao to the south, Ma Teng to the west, and Sun Quan too if Cao Cao take too long mobilizing his army to finish Yuan Shao), so he made the wise decision to move carefully and wait for Yuan Shao's inheritance problem to finish them internally instead of rushing his army and risk decimating a good amount of soldier.
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