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.
I think this may have been a case of that specific sword simply having wildly inflated secondaries. If I recall correctly, when I played during Wrath, +STR and +Hit were the stat kings for plate DPS classes (I remember all the guides recommending +STR gems in every slot and +STR enchants on everything) and secondary stats were, well, secondary, and inflated secondaries on a weapon weren't that big a deal. But now that secondary stats have so much more importance, I suspect that an "outlier" weapon like that just wreaks havoc with modern calculations, so that all the addon sees is that this particular sword offers +15 more Haste and Crit than everything else that drops.
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.
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But now, the Gear Advisor starts popping up, trying to get me to put the old 360 version Ring #1 into Ring #2's slot, since iLvl 360 is better than 350. Except I can't do that, because of the "Unique-equipped" modifier. So I click "Cancel". And then the window continues to pop up after every action my character takes, over and over and over, until I get rid of the old ring by vendoring, scrapping, or destroying it.
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