RE: Help requiring proficiency.
I mean, it's up to Egon. If we go with proficiency required to Help, then it makes sense to have Endurance try, with Ana assisting, since Advantage has the equivalency to +5 on a given check (+8 or so to the check compared to Ana's +5 by herself). I just think it's a weird that, mechanically, (in a good number of cases) an untrained character would have a better shot of succeeding at a task if they had the assistance of someone proficient in the skill than the proficient character would have with the assistance of the untrained person.
ETA: Too bad they're not small, then Gnash could talk to them.