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I'm sure others will chime in with specific advice, but it might help to know what you've tried. You can visit every card and still not end up rescuing enough people - it comes down to what you try to do during encounters along the way and how successful you are.
There is literally no scenario in which failing the gambit and then paying the increased price accomplishes *anything at all* for your quest. No other portion of Chariot does that, and (almost?) no portion of any other challenge either.
High Priestess has multiple Blizzard events. Huge Failure leads to a ♥♥♥♥♥♥♥ 1x Gain Any+ 1x Combat + 1x Pain, where Success leads to ♥♥♥♥ all, and Fasilure to 1x Pain
Meanwhile in The Hermit the same event just has normal 2x failure on Huge Failure.