A) leave him alone for five days. I have a feeder/water bowl that will last him that long, but I'm worried about if the feeder jams or something and no one is there to check on him, he'll be without food most of that time. Also, he's a very social cat and would definitely hate being left alone that long.
B) Take him with us. This is the one I'm leaning towards, but Im worried such a long drive + a new environment for a week + another long drive would be stressful for him.
C) Take him to a cat kennel. I really don't want to do this one, but will admit its an option. But it's expensive and this is also a cat that's been taken back to the SPCA three times before we got him; I cant imagine me dropping him off at a kennel would be a pleasant experience for him.
Also, will you tell me some of the ridiculous things your pets have done? My kitty learned the other day that hiding behind the curtains and jumping out at unsuspecting people is hilarious. :\