It's a great point about the daily driving. That was my only complaint when I drove the Duramax daily - it can be harsh - but boy, I loved that diesel engine torque. My F150 feels like a Lincoln compared to the 2500, and (for a HD truck) it rode pretty well. When looking for a new trailer, part of my hesitation was that I knew I needed to keep driving a HD truck to pull it, but just didn't want to tie myself to that tow vehicle. We ended up with a motorhome, and will pull the F150.
If you really want the smaller truck - and I completely understand and appreciate all the benefits of the 1/2 ton - then I'd humbly suggest buying a smaller trailer.
The 5.0 has been very good to me, but many like the Ecoboost as well for towing.