First problem: Set the candidate expression of the ability to look at the defining tag for each of those skills, separated by "|" which means "or".
Second problem: Do you have the ability showing a box for user text? Type some text in, then use the debugging tool to figure out which field stores that text, so you can refer to it in your script. It'll look something like this:
Render 10000
Code:
~ Around here do your stops
doneif (STANDARD STOPS)
~ Around here get your proficiency bonus
var profbon as number
profbon = THEMACROWHICHACCESSESPROFICIENCYBONUS
~ Around here apply the situational
#situational[hero.childfound[skHistory], signed(profbon) & " bonus when dealing with " & field[WHATEVERFIELDIDSTORESUSERTEXT].text, field[thingname].text]
Replace ALLCAPS with appropriate code, of course.