It depends a lot on where you live and what sort of driving you do. DRW is a non-starter for me because of two situations. One being tight city parking garages, which I have to get into pretty frequently. The other being off-road driving during camping and hunting trips - lots of narrow, rough forest service roads in the mountains in my part of the country. In both situations a DRW would really struggle. I also do a lot of driving in the winter on snow and ice and SRW is better in those conditions.
Happily, any trailer big enough to require a DRW truck would be difficult or impossible to get into the areas where I like to camp, so I've already got a built-in ceiling on trailer size.