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At level 80, I skipped Cataclysm and went straight to Pandaria. Even as my warrior leveled up, and that heirloom axe increased in iLvl along with me, Dugi still ranked that iLvl 87 sword higher. I kept picking up new 2h weapons, and Dugi kept rejecting them in favor of that Wrath sword. That's when I noticed that all of these Pandaria weapon drops, even weapons 20 iLvls higher than the Wrath sword, had secondaries under 20. So even though Dugi Gear Advisor is showing that a new weapon would provide a DPS increase, it still prompts me to re-equip that Wrath sword every time I equip a new weapon. Meanwhile, I've kept the heirloom axe in my bags, assuming that at some point its stats would once again beat whatever I had equipped, but nope, it doesn't, according to Dugi.
I've been having what is apparently a scaling issue caused by inflated secondary stats on some Wrath of the Lich King items. In particular, my Highmountain tauren warrior leveled through Northrend and picked up a green, iLvl 87, 2h sword. All of the secondaries were in the +25 to +30 range, and the Dugi Gear Advisor decided it was better than the heirloom 2h axe I was using. So I went ahead and equipped the sword.