The 6th gear top isn't a problem - the first 1300km in ours I did in one full day of driving - which was before we tried Snow mode so was entirely in Auto - and as 260DET says, on the open highway Auto doesn't show its issues - but I was manually selecting 6th at 100 / 110 cruise to keep the revs just over 2000 which stopped the trans from shuttling about with even tiny changes in road grade or wind. Indeed not the best for economy but MUCH better for comfort of driving (thats the V6 tho).
As far as braking in Snow mode I've braked late and relatively hard when driving "brusquely" and had no issues with it - ie. havent had cause to think at all about what it was doing and how.
The one thing I do wonder about is kickdown behaviour - my wife has said that she's had foot to the floor and it wouldn't "take off" - ie. kick down. That's around town - the situation is planting it after some yoyo has done something stupid in front and she's gone to take off once they were out of the way from low speed. I haven't checked that out or experienced it myself but it makes sense Snow would be a bit "conservative" in that situation.
Second gear takeoff still gives plenty urgent enough launch - but yeah, Auto is very gratifying off the line
Snow can tend to be a good tamer - I drew some looks the other day when what was meant to just be a no mucking about pull out from a parallel park street side bay when a gap presented ended up being a sports car like LAUNCH in Auto. Snow mode would have made it much more conservative and drawn no attention.
As i've mentioned elsewhere I program the ECU in our Falcon myself - including transmission shifting - so tend to be possibly a tad too analytical of it all
(the Falcon has a pretty huge cam so wont even idle without custom tune).
As such tho, its disappointing how flawed the Auto mode programming in the Cherokee is - with our Falcon I've managed to balance all the factors like timing effect on torque at various loads and revs as related to how that reflects on shift points - ie. balancing them all against each other (INCLUDING adjusting how quick/hard the shifts occur) - over full rev and load range - WITHOUT a dyno - better than the Chrysler factory people seem to have managed with the Cherokee - which seems really wierd...