Yeah you should have no problems with putting it in the back of the truck. I bought a bed extender when I went to pick up my ride 115 and didn't need it. Probably could even go a couple feet longer and still be good.
I think the rudder would be dependent on which kayak you get, where you are using it and maybe your paddle stroke. I've only had the ride out in moving water and I see no need for a rudder at this time. Had a cuda and lure 11.5 out during demo days and didn't see a need for one on the cuda but would not have bought the lure without one, it didn't track well for me.
Flyfisher is spot on on the anchoring in my opinion