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Looking for an interpretation here.  Gloves of the Healer and Healer's Armor (and other similar items) have a property that when you use a power that allows an ally to spend a healing surge to regain hit points you grant a bonus to that.  1d6 extra hp gain from Gloves of the Healer / Enhancement Bonus added to healing with Healer's Armor.

If I use a power that allows an ally to use their second wind, then does the property from the item activate?  I'm allowing them to use second wind and a healing surge by proxy. 

No.

To be more precise:

1. Second wind isn't actually a power (although I wouldn't be surprised if the Character Builder makes a power card for it).  It's an action that lets you spend a healing surge and gain +2 to all defenses.  In fact, an errata had to be released to update the Dwarf's racial power in light of the fact that a variety of in-rules options allow you to recover second wind multiple times over an encounter.

2. Gloves of the Healer and the like applies to powers that let the target spend a healing surge.  A power that triggers second wind is not a power that lets the target spend a healing surge; it is a power that triggers an action that lets you spend a healing surge (all powers involve actions -- even No Actions -- but not all actions are powers).

3. Rules-as-written, even if Second Wind was a power, it takes a rather convoluted reading to allow the Gloves of the Healer and the like to allow a power that activates a power that lets you spend a healing surge to transfer the benefits of the items down the line.  That said, the DM does have the final say on the matter, so if he's fine with it, then that's that.