Sure you can do it but that's a pretty deep boat for more than barely occasional trailoring. Given the size of your tow vehicle and the size of the required trailor and the need for steeper than normal ramps and a power cable ability to let the trailor down into or up from the water while the truck stays at the waterline, figuring a light way to step the mast would be no more difficult or expensive, maybe less, than converting to deck stepping.
For stepping, an A frame just a bit ahead of the partners, braced on the gunnel and firmly stayed fore and aft only needs to be about 6' higher than the place at which you can control the mast when verticle and this can be a bit below the balance point if you learn to control the load. Alternativly if you're going to launch near a bulkhead, a simple little fold-up crane and ginpole mounted on your truck could do. Finally, I've seen some pretty hefty catboat masts where the gin pole actually folds up from the trailor, tailed to the truck, but I think your boat's keel will put her up too far for that to be practical.
Against that, to deck step you most likely need a mast of heavier wall sections and may need to have the stay pattern professionally re-engineered. The actual raising and lowering of the mast will put considerable strain on the step hinge and you'll be wanting some sort of jack pole or A-frame that starts at verticle when the mast is down and that the hoisting line can go over to give some advantage. As I say, by the time you're done, better to think through something with the existing rig as you'll not trailor much anyway.
G'luck
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