Gil has a rate-up next year, to the best of my knowledge Jack's next rate-up is in two years, so I don't think you have that much of a choice here. Just go for Gil in 2019 year and Jack in 2020, unless she spooks you first.
Personally I'd go with Jack, just because Gil is reliant on crit stars while Jack can generate them. One is simply easier to use than the other.
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