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It might be possible, considering that certain Actionbar Addons can put custom text on Actionbar Buttons and others (like BindPad) put custom text on Abilities (in it's own GUI).
Basically all that needs to be done is write an Addon that creates a FontString containing the Item Info and make the ItemIcon it's parent. This would probably have to be done seperatly for the Inventory and the Character Equipment Screen and for every other element of the UI you want the TextString shown in (even other Addons, Altoholic for example), as it's not possible to write directly to the Icon.
Else just an advice for upgrading gear: Don't ever go for ilvl! I have several items that have a higher ilevel but aren't better than my current item. Also you want to balance your stats, for example if you're a priest you have to think if it's worth to loose 40 spellpower if you get 70 MP5 for it. So just going for ilvl isn't good.
Remember you can make the ilvl be shown in the item tooltip (think it has to be enabled in the interface options).
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