Kennel vs. friend coming by vs. Stay in another home

I'm a pet sitter so I understand all of your concerns completely.

I've done this in the past with some of my clients.  Since Dweezil still needs more than three visits per day, how about dividing them up.  Have your friend come by for some and have someone else for the others.  Maybe your neighbor could check and make sure the doors are locked and everything is OK before bedtime since they are right there. 
 
This way too, it's people you know coming over and the puppy can stay in it's own environment.

Hmmm I will definitely consider that idea -- have you had any experience with kennels??  It just seems that the kennel is definitely the most worry-free and least complicated, but every single situation has its pros and cons.

Here's my experience with leaving my dogs, for what it's worth:
 
The first time I had to leave Loki, he was 8 months old and he stayed down the street at a neighbor's house. They have different "dog rules" (ie they allow their dog on furniture), but when he came back, he still knew our house rules. He was with someone I knew and trusted. I could call my neighbor for daily updates, so I felt better about leaving him. And he got to play with another dog all the time, so he was tired and happy when I came home!
 
The next time I left, both Loki and Odin were kenneled for the first time. I checked the place out first and saw that it was clean and the people were really friendly. I was still worried, but I was able to call the kennel for updates and the boys absolutely loved being there. I knew they had 24 hour supervision by trained professionals, so I felt good about it. Personally, if there was one person there that was rude, but the rest of the staff seemed really friendly, I wouldn't be too worried. That person may have had a bad day, but if the kennel is clean and has a good reputation, that's the most important part.

My best friend is a dog sitter and takes care of the dogs in her home, so that's where Gracie spends her vacations and she LOVES it. If I didn't have Goldy to watch our dog I would probably opt for a really good, high quality kennel. I would worry about our dog getting bored with just having someone come visit and walk her a few times a day. At least at the kennel I'd know she would have supervision, dog playtime, and walks.

Well, from a dog sitter perspective kennels are my competitiion.  So, speaking strictly from a dog mom point of view. 

I like the idea of the dog being in it's own home.  Also, being young, I'd be worried about contact with other dogs and what he might pick up there.  I've had clients who have actually called me AFTER having a bad kennel experience, as in the dog came down with something right after. 

I also like that familiar people will take care of him and even if he has to obey certain house rules if he stays somewhere else.  You could always talk to the person and let them know what you are working on with him ect, I'm sure they'd be fine with that considering it's someone you know.  In a kennel they don't get much time out for fun, etc. 

There are pro's and cons to each. 
 
The dogs I sit for that need multiple visits, I go in the am and afternoon, her in-laws come at dinner and bedtime. 

I would let my sis takecare of my baby gal if I'm away.  For one thing, god knows what they really do with the dog at the kennel.  Ok so there may be a few that's good, reliable, and does everything right.  I just would find someone I trust and have them watch the dog in a home enviornment.  []

It is definitely sounding like home environment is winning (and I agree) -- but now really my question is whether it should be here at home, or at the neighbor's house down the street.  If it were here, I would probably have a neighbor take her out mornings and a friend come three more times during the day.  It would definitely be less of a worry to send her to the neighbor's house, but I'm wondering if that might be bad ...  They don't pick up their poops regularly ... and I'm so anal, I'm afraid that my requests would be too much (can you check her after every walk for ticks, can you make sure she stays off the furniture) ... and also, their doggie waits about 10-11 hours during the night to potty (and is actually roaming the house) -- he's Dweezil's age!  Dweezil is only waiting about 8 hours a night ... would this stuff mess her up?
 
They do love playing so much, though, and this way she'd be having so much fun while I am gone ... and it is only for 5 days.  I'm not sure.

we havent been on a vacation since getting dogs. however, we put our cats in a kennel once when we were on vacation and they did really horribly even though we trusted and knew the people at the kennel they were at. since then we have only used a pet sitter for them, but cats are easier in that we only had to have the sitter come by once a day to clean the litter box and make sure they had enough food/water (they free feed). the added bonus was that she (the pet sitter) would check the mail and water the plants.

if i had any reservations about a kennel i would definitely find another one. i have learned over time to trust my gut instincts. there have been too many times that i had reservations about one situation or another and went ahead and did whatever it was and then regretted it later.

I'd pick #3 -- if the neighbor is a generally competent person who you can trust to treat your dog well, even if not exactly as you would treat her, that sounds like a great set-up.  I'd love to find someone to trade dog-sitting with.  We used to have friends that we traded with 'til they left town. They have different standards for dogs than we do, but in general they are nice to the dogs, take them for regular exercise, & feed and care for them properly.  Good enough for me for vacation lengths of time.
 
Learning different house rules is generally not a problem. In this case, dogs being bad at generalizing works to your advantage. They learn that "in this room, in this house, with this person" I am allowed on the sofa, for example.  But that doesn't translate to being allowed on the sofa in your room, in your house, with you. 
 
Roscoe knows different rules for 4 different houses, and they are as varied as being allowed to dig vs not dig in the yard, allowed on the furniture vs not allowed or only allowed in certain situations, allowed to run and chase in the house vs not allowed, etc. And he is not the world's brightest dog, either. (I love him, and he's wonderful, but I cannot claim that he's aussie smart. LOL!) 
 
As for your parents, just ask them.  If it is a once in a while thing to return a favor and you can assure them you would take full responsibility, they might be willing to go for it.  []
 
Good luck!

I'm definitely going to go talk with my neighbor when I take Dweezil for her walk -- I really don't feel comfortable with the kennel idea, and I figure that this neighbor's dog is incredibly happy and friendly and healthy looking, and this would be much better than her being alone all day.  If it doesn't work out with the neighbor, I think I'm going to have my friend watch her -- I don't think 3 times a day is too little just for a 5 day span, and I'll ask her to stick around for a few hours for one of the multiple visits.
 

In this case, dogs being bad at generalizing works to your advantage.

 
Thanks for that, jensw, that does make me feel a whole lot better!