I have taken my buns with me to my parents’ house a few times, about an 8 hour drive, and they did well. I think some of it depends on the personality of the rabbit, but as long as he’s not extremely skittish and opposed to change, he’ll probably be fine with the car ride and new location.
I have also left my buns at home with someone to come in and feed them twice a day, but they don’t get any out of cage time (they have a large enclosure though), so both work. I would definitely recommend hiring someone to come twice a day if possible though if that’s how often he’s used to eating. You could probably make once a day work though if he always had lots of hay available.
It’s really up to you – there’s no right answer. As far as car travel, the crate doesn’t have to be tiny. For medium sized rabbits, under 10lbs or so, a typical cat carrier is fine. I don’t leave water in there because it’s messy, and because my rabbits don’t drink very much anyway. I do give them some romaine lettuce for longer trip because it contains a lot of water, but they rarely bother with it.