People probably don't understand how this site works and I feel aweful for Milagros.
This site gets all it's data from the World of Warcraft Armory and stores a snap shot of it. It also grabs the date of when it last looked at the WoW Armory and did this.
Up to date is simply a timestamp of when it last looked at the WoW Armory. However if the WoW Armory is behind and not updated, then obveously the data Heroes grabs and updates will be out of date.
So if you goto wowarmory and look up your character and that gear does not reflect your current gear, do not expect this site to magically have info on your ingame gear.
I would imagine the WoW-Heroes team could impliment a simple check to see when the last time a piece of gear actually changed in any way shape or form and mark this date. Then it could show when WoW-Heroes last updated the snapshot and when it last saw your character with a change. Idealy if your gear hasn't changed in awhile it could raise the flag to the GM/RL that maybe its not current.