Which vehicle to take to Winter Park?

We're going to be driving from Chicago to WP the last week of March. The
vehicle choices a

99 Dodge Durango 4WD with 85,000 miles. Drives OK around town, but Durango
trannys are notoriously dicey after 60-70K. Would hate to be broken down
somewhere in eastern CO with the kiddies in the car. Also, less than
confident about it's performance on those long grades.

03 Chevy Silverado 2WD pickup. 10,000 miles. Extended cab seating is going
to be much less confortable. Mechanically, it's fine. Traction in a 2WD
truck ain't the greatest, though. A little nervous about encountering slick
conditions on Berthoud Pass.

Any thoughts would be appreciated,


Jim