Aly. While I know the temptation is great to go the petsitter route...Reece gets to stay in his own home, familiar surroundings, etc., I have learned of too many tragic experiences lately with petsitters. Dog's getting out of the house or yard accidentally, getting into things in the house that cause illness or injury, even one case where the petsitter (this petsistter was a FRIEND of the dog's guardian who the dog knew and liked) brought a male friend along with her AND his dog. The dog being petsitted became so protective, she bit the man and was eventually "put down" after a long court battle! I know you may feel that Reece will be scared and lonely at the Day Care center. But as someone who works at a boarding kennel, let me assure you that if the facility is a reputable one, Reece will be safer, and probably happier, there under close supervision and in the company of other dogs. And it's only one night. I know how torn you must feel. Of course, if the person is someone you really know and trust, and someone who knows Reece and who Reece likes, that MIGHT be different. If I read you correctly, this person would only come once or twice a day to feed, walk etc? Not living at your house? Often times, the dog being petsitted is LONLIER at home without the guradian present...."Where's Mom?" Becoming frantic, etc. I know it's a hard decision. But, to err on the side of safety, I would board at the Day Care center. Let me know what you decide!