How I would rule it would be asking how original was the idea at the time provided, what was the narrative obstacle the group was trying to get past, how logical was it to have the required equipment on hand, and what were the potential results to the overarching story were it to succeed and fail.
So for instance... if the character doing this was a crazy inventor Artificer trying out their wacky new invention, then that character would have a much easier time of it because from my perspective, this is the job that PC was created to be able to do. Likewise, if the group has pressing matters elsewhere and every single member of the party had a way to bypass the obstacle of the water in front of them except for one of them, I probably would not care to bog them down in a pointless potential "drowning scene" right now-- it would have just as unneeded a dramatization in the story that slows things down for no actual gain as making sure characters stop to go to the bathroom while adventuring. Do we really need to play out every single time the platemail-wearing PC having to take a 30-minute break to get in and out of their armor just to go poo? No, we just handwave it because it is not important to the story. Likewise, do we really need to play out the experimentation on the buoyancy principles of armor and air just so the group can keep going on towards their actual concern? If they answer is no... then we just maybe do a quick check, acknowledge the creativity of the idea, and then move on.
BUT... if this is just one of many important parts of the current situation the party finds themselves in and is an intricate part of the plan they are undertaking right now... then of course this idea will take front and center on the actions of the group and who knows how many checks will be needed to overcome this obstacle? But at the end of the day... getting a precise "real world" number of waterskins won't be necessary... merely just that the characters involved did or did not figure the answer out.