I have done the weapons system and it works pretty well, except for a couple things
You turn off the item trigger, move the item off the hero, THEN evaluate if he has a weapon. This stops the item manipulation from getting in the way. If he doesn't, give him back the item. If he does, then do nothing, and give the text. Then turn the trigger back on. This works with Item levels and classes. Custom values are a bit harder but will work