Brian Mc Cabe
There are those who look at things the way they are and ask why . . . I dream of things that never were and ask why not
A rule of thumb I use:
Trading away does count as "losing." Otherwise, for example, Zoey can never fail her personal story if she simply gives her Cross to someone else so that she never technically loses it.
Obtaining via trade does NOT count as "gaining." Otherwise, any personal story that can be passed by gaining unique items can be too easily passed by a single repetitive trade.
I rule that if Zoey trades her Cross she fails her personal story, so this is a good example you're using in answering this question