Everytime I go on vacation my dog gets sick...I am about to leave, any

Captain

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suggestions to try so he stays healthy? I am going to be going on vacation in the near future. I will be gone for a little over a week. My 10 year old lab mix has never done well being away from me. I have had him since 4 weeks old (his mom got hit by a car, unfortunately) and appears to get severe separation anxiety when I go on vacation.

I used to board him, but it was worse. He doesn't eat and drink, has had to get IV's and taken to the doggy hospital...and this has been with more than one boarding house.

So now I leave him at home in his comfort zone, free roam of the house. I have another dog but he doesn't seem to care if I'm there or not. And a friend that comes over to housesit and dogsit. The dogs are familiar with him and always seem to enjoy him coming over.

But my lab mix still doesn't do well when I leave. The last time I left for a week in the summer he was so sick 3 vets told me to put him down. He was severely dehydrated and they said his kidnies weren't functioning right and he couldn't keep food down. Me being me would not put him down, just gave him a bunch of TLC, the vet gave him some shot (on two separate visits) to help hydrate and help him keep food down and he bounced back.

What can I do this time around to keep him healthy while I'm gone? I know he is in good hands with my friend and in the house, just need to make sure he eats and drinks properly and doesn't get depressed. Shoot, I never want to go anywhere because I worry about him so much. Please help.
He is very familiar with my friend because he comes over once or twice a month and has spent one on one time with him. The vets just seem to chalk it up to old age and those are his problems. I have always worked (with the exception of a month or two) in the ten years I have had him. But he knows when to expect me to leave and when to expect me back.

Last time I tried to give him pedialite after I got back home from vacation but he wouldn't drink it. I thought about putting it in his water while I am here to get a jump on things. He is on prescription food for his kidnies now, too. I just don't get it...he has the comfort of sleeping in my bed, his buddy (the other dog) and basically gets a little vaca from everyday life when I go away.
 
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