Kayaks should fit the 26RR, 3 four wheelers may be pushing the room limit but may work since one is a 50cc. The work and play is a heavier unit and the dry weight is at the limit of the F150 4x4 rating. The dry weight on the 26RR is about 2500 less, I have know problem pulling it with my F150 and Harley loaded.
2013 F150 5.0
2011 Harley Touring