When I decided to get out of my 2011 F150 Limited 6.2 (loved it!) I was set on getting the new F250 with the diesel. I also tow a car hauler about 6 to 8 times a year however my trailer is an aluminum open style that's about 2000lbs lighter than yours. But other than that the truck was going to be my commuter vehicle that I'd put ~20K miles a year on.
I really didn't like the look of the front end of the new F250's but overall they seemed like an absolutely awesome truck. I wanted to make sure I could live with it long-term so I traded my good friend for his for a week. I drove it for about a week and several hundred miles, always unladen. At the end of that week I knew 100% there was no way I was buying that truck. The ride was a complete beat-down. If I was constantly towing then hands down I'd be all over it. For commuting it sucked.
Then I started considering the Raptor and even though I don't use it as it's intended, I loved the truck, especially the looks (I know, shallow). When I do tow it's 'pretty ok'. It hauls the trailer fine but requires accurate placement of the car on the trailer for optimal balancing.
Overall, the best thing I did was drive that F250 for a while so that I'm now not always wondering whether I should've gone that route instead.