Vacations? I think I remember what that is

We have two Basenji dogs, one female (Jezebel) and one male (Oli) and both are complete opposites while being exactly alike! Our biggest dilemma is when we take vacations because while they are Basenji and have very similar character traits, the fact that both are rescues and their lives are unknown to use before they lived with us makes them both very different.
Jezebel’s past is unknown but she had the fortune of being with another rescue group that truly helped her. She has no issues with separation, crating or aggressions at all. Our other dog Oli is another story. He is the complete opposite – has separation issues, can’t be crated and although he is not food aggressive, he does try to be the dominant one at all times.
Oli is great in our home during the day. We rarely see any damage while uncrated and unsupervised. He tends to destroy his own toys and if we leave the laundry room open, there is a chance that he will push over the garbage. All in all, he handles being alone from 10 am until 3 pm pretty well. We see problems when my husband and I leave over night somewhere.
We had my brother in law take care of him during our last vacation – 3 years ago and yes it was the last time WE went on vacation together! Oli likes my brother in law plenty! Give him lots of lovin’ and sits with him and even pays a little bit of attention to his commands so we didn’t see a problem in leaving him with family members. Besides for my brother in law it would be a welcome break for his family because they live with their in laws – one big happy family… So begins the horror story.
Oli was fine the first day but noticed that we did not return that evening or the next morning. Orly (my brother in law) recalls seeing the anxiety building. He would pace back and forth from the door to the kitchen. An evening away at the movies ended in shredded kitchen towels. As the week progressed the damage increase and so did the whimpering and pacing. Thursday came around and Orly bailed on us. He could not take the crying and destruction any longer and opted for coming around to check on the dogs in the morning, afternoon and evening for a feeding.
When I returned to my house it looked like there had been a reenactment of the Tasmanian Devil cartoons in my living room and kitchen. Oli managed to push a dining room chair over to the counter and spent quite a bit of time up there. He shredded our curtains, the speaker covers on the stereo, the knobs on some of the kitchen cabinets, the dust guard on the refrigerator, the plastic flowers in the vase on the dining room table… the list goes on and on. There were items that were no longer identifiable – we still don’t know how much he destroyed, but every now and then when we move a large piece of furniture we find something – mauled.
I resolve to never leave the dog alone again – big mistake, I know. Well we are planning a weekend getaway and I will be leaving him at a doggy hotel for the weekend. I don’t like kenneling at the vet only because I know that he gets very stressed in a kennel. Saturday we have a “play date” scheduled where I will visit with him and he gets to run and play and get to know the other dogs at the hotel and if all goes well – which means that if the administration likes him, then he can stay. I’ve got my fingers crossed, but with Oli – you never know what you’re gonna get!