Opinions are like noses, everyone has one, mostly the opinions are dictated by personal experience and what worked and what turned into a disaster. So, all that said, it is my belief that you start out as you mean to go on. If a weekend retreat is your normal schedule, then pop Bruce into the carrier, bring along his litter box and anything else that his smell on it, so he has something familiar to associate with and off you go. There is no need to wait or go by yourselves and leave him in the care of someone. Keep to your weekend routine of feeding/playtime the same as your weekday one. The more normalcy you can bring to the trip the better. Now, understand that every animal is different but in my experience, if you follow my suggestions, keep things calm and routine so he doesn't feel stressed, give him lot's of encouragement & some special treats that he only receives at the weekend house, I honestly don't see why you can't do this successfully. Paws up @HelloMissKitty suggestion for keeping the carrier out with the door propped open and tied back so it doesn't slam closed accidentally & scare him and a cozy blanket inside. This way it will not be a scary thing. You can also feed him treats in there to help him acclimate if you feel it necessary or toss a toy into so he'll go into it on his own. Anything that makes the carrier a happy place. Best of luck, let us know things go?