Whether it'll be easier is going to be pretty subjective.
My tailer sits quite high ("off road" package, yo), and my driveway is also an inch or two higher than the street. I have to be parked on the street when hooking up (driveway barely fits the trailer itself), so I end up with the vehicle wheels lower than the trailer wheels, and a trailer sitting high to begin with. If the LX is not in HI when hooking up, I simply can't get the trailer on the hitch and off the trailer tongue jack; the jack runs out of retraction room before the coupler connects to the ball. So in my case, I hook up with the LX in HI, then drive out and park on the street in N height, and set WD tension.
In level campsites I can usually hook up in N, but HI just makes it easier.