Vacation feeding advice (on various topics) desperately needed

I will have to be away from home for 6 days (5 nights) in the near future.  I will have a cat sitter come once per day for sure, and she may be able to come twice per day on some days, but I don't think she can come twice every day.  My kitten will be almost but not quite 5 months old.  She will be in a room with her "big brother" most of the time, and separated long enough to eat their dinner (the sitter will stay while they eat) because they're both food hounds.  For feeding purposes I would've liked to keep each of them in a separate room, but they love each other to death and would be miserable apart.

I'm trying to figure out solutions so they can have at least two meals a day (the kitten currently eats three, but for a few days there's no way I can make that happen).  To that end, I have a few questions.

FIrst, I will probably use at least one and maybe two automatic feeders.  (Leaving out a big bowl of food wouldn't work as they would just eat the whole thing and make themselves sick...seriously, they *love* food.)  Is there any option for leaving food sit out for 5 days other than dry kibble?

Next, my big boy kitty is stressy and has had a urinary blockage in the past, and the only thing that keeps him consistently unblocked is Hills c/d.  Everybody normally eats canned food only, but they've had bits of dry here and there and have no problem with it (they aren't finicky kitties at all).  As long as my kitten gets her usual canned kitten food for her evening meal (the sitter will do this) and my big boy his canned c/d, would it be okay for my kitten to share dry c/d food with her big brother for her other meal for these few days?  (If this isn't okay, I guess I'll have to keep them in separate rooms, which would be sad.)

Next, does anyone have advice on transitioning my kitten temporarily to a two meal schedule?  Should I start gradually making the meal that will be eliminated smaller and the other two meals bigger?  If so, how far ahead should I start doing this?  Anything else I should do?

And finally, does anyone have recommendations for automatic feeders?  I have an old Pet Mate 5 Meal Feeder but because it's old there is a problem with it where the tray only rotates part way.  I understand they resolved this issue a few years ago and the I've heard the newer ones are better.  I found a fix online for mine but not sure if I have the skills to fix it.  Depending whether I can, I will probably buy either one or two new automatic feeders and set them to open at the same time so neither of the  the chow hounds can't bully the other out of a meal. ;-)   Are there feeders that are better than the Pet Mate 5 Meal?  I had a Le Bistro for a short time, didn't think I'd need it after my dog died since the kitties eat canned so I gave it away...now I wish I hadn't.  I found lots of other different automatic feeders on Amazon that I hadn't heard of.  Any recommendations would be appreciated. 

Thanks much!

I would say taking them to a boarding kennel with a separate cat area would be easiest. It usually costs more to have someone come to your house twice a day. Plus boarding facilities are used to following individual special feeding instructions. I work at a facility like this and every pet had its own food and instructions. It all gets put on their feeding card and is followed exactly.

Thank you very much for taking the time to reply!  Unfortunately boarding is not a possibility, for various reasons.  Among those reasons, I have four cats total (only the two mentioned present a vacation feeding problem though).  I wouldn't be able to afford to board all four, and if I boarded just the two I'd have interpersonal issues (fights) just like I did when one had a urinary blockage and spent a night at the hospital.  Also, my sitter is my sister-in-law, so there's no cost involved there.  This isn't a fun vacation, this is a have-to-go situation despite it being horrible timing for me and for the cats (I'd rather go when the kitten is much older...like no longer a kitten), and I need to keep it as inexpensive as possible.

So that being the case, I'd still be interested in opinions on the various questions posed in my original message.

Any advice appreciated!

The Hills c/d should be fine if the kitten eats some. You wouldn't want him on it long term because the kcals and calcium are lower. But the c/d just has adjusted mineral levels for cronic urinary problems from what i can see. If you aren't sure call a vet but i would say yes.

And if you don't want to but more feeders can your SIL just put out a days worth of food at a time when she comes in the evenings? Some may eat more and some a little less but they should be fine for a week or two. Good luck