Based on what I have seen the tag does not provide the *. That * represents that you have added "situational" text to be displayed on the Pick.
Try this:
Code:
doneif (field[gIsAttuned].value = 0)
foreach pick in hero from BaseEquip where "ToolCat.Gaming"
perform eachpick.assign[Proficienc.Tool]
perform eachpick.assign[Hide.Tool]
perform eachpick.assign[Helper.Advantage]
#situational[eachpick, "Advantage to all gaming related rolls.",field[name].text]
perform eachpick.pulltags[ProfTooDbl.?]
nexteach
perform hero.pushtags[ProfTooDbl.?]
Note I am not near HL so didn't test this but pretty sure it will work.