Instructions for dogsitter.....

I would write up a schedule of exactly what you want done, then write a list of some of your dog's favourite games and activities. Also write down any quirks your dog may have and advice about how to deal with them. If there's anything you don't want him to do (no dog park, no off-leash walking, no people food, whatever), write that down as well.

First make very sure the parents are on board with taking this responsibility as well.The boy could come down sick,what then? Second for a young boy iwould write out a very specific schedule.Even youngsters with the best intentions can get side tracked.Give him a copy,his parents and put one on your fridge.It would alsobe better if the dog stayed at his house,easier to remember the responsibility.Also if there was a problem with the pup,noone would be there to notice right away.

I'd get a webcam!   I got one for the same exact situation - our dog walker stayed with Slick while we went away.  We had video conference calls with her a few times a day (we're nuts, I know).  It worked out incredibly well for us though. 
 
I would just ask the kid to hang out at your house as much as possible.  The rest of it (playing, attention, etc) will just happen as long as he's there.  Oh, I also challenged Jackie (our dog walker/sitter) to teach Slicky a new trick by the time we got back.  Each day when we spoke to her, we saw his progress with the trick and knew that he was getting lots of QT with her!

Maybe a typed-up chart, with a list of all of the tasks you would want him to do on one side, and boxes for initials on the other? When I worked with an in-home petsitting company sometimes clients would leave things like that and I loved it because we knew exactly what was expected.
 
Since Rudy sounds like a smaller dog, maybe pre-portion his meals into little Ziplock baggies or Tupperwares? Just so the sitter wouldn't over or under feed him.
 
Another idea would be to leave all the 'stuff'-leash, collars, instructions, any meds, food, bowls, treats, ect. all in one spot, like a kitchen counter or table. I have been in houses where the dog food would be in the most UN-obvious spot of my entire life.
 
Make sure you leave a list of phone numbers too. Not only yours, but the number for where you are staying, the vet's number, and a number for family member or someone trustworthy who lives close that could be reached IN CASE you couldn't.
 
If you have time, could you possibly have the boy come spend a couple hours with you and Rudy before you leave? That way you could show him everything, and give him a good chance to ask questions too.
 

You guys are the best! Great advice from everyone as always.

I'm definitely going to type up a SCHEDULE for our puppysitter, I love that idea (better than just a list). And the idea of challenging him to teach Rudy a new trick is GREAT!

I did call the boy's mom before offering him the job. She and I have known each other for years, and we're friends. They are HUGE animal lovers, and gave me great help and advice when we first got Rudy. Also across the street from us is a woman who works at the local Humane Society, so she'll be a great help as well. I'm even going to give him the number of our friends around the corner who offered to watch Rudy as well (but they were having 30 people over for turkey dinner, and I thought it would be too much chaos) --- so he can call them if he decides to take a break, or if he goes hunting or gets sick, etc.

I'm soooo nervous, leaving my puppy!!! Next year, we'll probably take him with us on this trip. But he's in a terrible chewing stage right now, and my brother and SIL have a brand new kitchen that I don't want him teething on!

I bag up all food with labels (stick the label in the baggie). Then I line up the baggies somewhere obvious with everything else that will be needed for the petsitter.

I make the most anal writeups EVER. I include all commands required to get the dog through doors, inside from outside, in the car, back from chasing something, even in the tub. I include the fact that Ben has to be commanded to eat, and where everyone is used to eating and sleeping. I include what should be included in everyone's kennel/crate.

In another folder, I have emergency information for EACH dog. Vet records, meds, emergency number for me and two other contacts that are familiar with my dogs and my routine, description of dog and tag #s (and microchip #), and two good pictures - face and side view. I also have written down who to contact about the pets and livestock, should anything happen to me - either temporarily or permanently. Each dog's emergency information should include information on where the dog goes should anything happen to you! Relatives do unbeliveable things when tragedy strikes.