Yes. Our toyhauler is probably around the range of yours once loaded up (without a toy, we didn't have a toy when we had an F150). We did that same upgrade, F150 to F250, and the difference was like night and day. If we weren't planning on upgrading to a fiver soon, we'd still have the 250.
Our F150 was set up properly too... WDH, new tires, airbags, pretty much everything everyone on here recommends to set up an F150 properly. It was just miserable in the wind.
And, for the record, I had to drive our 250 to work sometimes, it was about 20 miles each way, in traffic. It was fine for me, as a 5'3" female. If anything, it was a bit fun, much easier to see all over the cars when driving it! The 350 dually we have now is a bit more cumbersome for rush hour traffic :)