Honda will be easier to live with, by far, as a DD. Even new, those Jimmy's didn't fare well. It's like GM went through some cheapening around that time. They aged rapidly with regular use and seemed to nickle-nag their owners. I saw a lot of friends buy them up when newer because they looked so sleek for a compact 4x4, but the ruggedness wasn't there.
I've lived with a couple of crv's. Yes, the dual-pump fluid needs to be swapped every 30k. It's easy to do. Internally, t's a similar architecture to jeeps "guadatrac" limited slip arrangement. If the front spins out, it will bite and kick you forward. It is effective in the snow and in the slick rain, and stays out of the way the rest of the time. Keep the fluid changed and it will be happy. IMO it's a superior system to the haldex arrangement which you see everywhere else, Ford, Volvo, etc.. The honda engine and drivetrain will be much easier to live with as well.
The only reason I'd consider the Jimmy is just if you have a thing for RWD vehicles from a driver's hobby point of view. If the vehicle "means" something to you. CRV's are ubiquitous and can be a bit of an appliance, especially newer ones with the CVT, which is what my wife drives now (LOVES IT, her favorite car she's owned, and admittedly, it's really good at what it does). I don't like to admit that the "image" of a car matters to me, but to a degree it does, and the CRV doesn't do it for my own tastes. I'd eventually consider selling it and seeking out a volvo wagon or somesuch,