I bought the 99 drw in 06 and the 99 srw in 01. Having owned both for quite a while have found ups and downs for both.
For towing heavy the drw hands down wins. The stability in the driver seat with the drw is night and day better compared to the srw.
In snow would have to say the drw does better than the srw. We had 17 inches of snow a few year ago and I got through it without 4wd but had to lock in it of course to get the srw unstuck in my driveway. The drw did have new Michelins at that time though.
As far as drive thru's never had an issue with the drw. The drive thru's at banks are the toughest as they only leave a couple inches on each tire in most cases. Used to park the drw in the garage got about an inch on each side.
In terms of mpg the srw is better. For tire cost and rotating of course the srw.
Another draw back for my drw is because it's used for work it's commercial so there are some roads we can't go down. Last Winter in Boston it was as little tricky at times with the drw but it worked out just fine. One road we thought about backing up but made it through as we scraped snow on the banks on both fenders.