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I did 10+ hours with my puppy but it was broken into two legs and he was in cabin with me, so it's not really the same. He was fine, though! Pretty much slept the whole time.

I'd say see how well they cope with their flight before you make any decisions about future frequent flying for them. 16 long distance flights per year sounds like a lot of stress and risk to me, though. I'd especially think about leaving them home during the hotter parts of the year, as poor temperature control is one of the big problems for dogs and flying.

Different airlines have very different safety records where dogs are concerned, so that's something to be careful about.

I think you are supposed to have a food/water tray inside the crate? If you put ice in there instead of liquid water it'd probably hold up to travel better.
 
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