Ill be blunt, you're trying to micro manage your players a bit too much. HL isnt a do everything for you.
I would keep a listing of item numbers and descriptions, and then only give the actual item when it is identified.
Shadow has a few useful adjustments for modifying item text/output, but blank ITEM ## seem to be the best way of doing it.
Also keeping track of initiative via the TC isn't something that I would recommend. I have found that either a
Pathfinder Combat Pad or Tent folded note cards are the easiest way of tracking initiative since it is so fluid.
I could probably work with you some more but the forum really isnt a place for GM guidance.