1. I don't know what you mean by "vintage watch servicing". My Watchmaker services all pieces that come in the same. He treats new and vintage pieces with the same level of care. There is a thread here regarding how often a watch should be checked where Archer explained the basics of gaskets and how often a watch should be vacuum tested.
2. If it matters as in sealing properties? Nope. I hope you're comparing apples to apples and not a diver to a dress watch. I guess it matters only if the case is made out of gold, since gold does not corrode easily and it does so only under very specific circumstances. All well-maintained watches will have no trouble keeping the moisture out if they had water resistance to begin with.
3. They matter very much. I guess the crystal is the only one that sort of gets a pass if it's of the proper dimension as there are quality non oem crystals but don't take my word on that one. Correct crowns matter. Proper mainspring matters and so on.., if you're referring to other parts not involved in the sealing aspect.
4. Age is the biggest factor. Due to corrosion and other types of damage to the sealing surfaces a 70 year old watch will not seal as good as new one. One key thing to remember is that this kind damage can be microscopic and therefore hard to spot.
I have a 50 year old diver that has not seen any water since in my possession. I'm guessing the former owners didn't subject it to diving either, or took great care of it since the dial lume shows no swelling and movement is very clean.
I'm also guessing that a proper maintained vintage watch that had WR from the factory and has no damage to the sealing surfaces will survive a splash or a drop in the water. Again, don't take my word for this one. For example, If it rains outside I won't wear a vintage piece therefore I don't know what the odds of survival are. Your problems sound like they would be solved by either having a beater or a modern reissue of a vintage watch and that's why I own a SKX.
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