Hi Jake,
Trailering is a very important part of taking care of your boat. Hull covers are great. A wood floor in the trailer is a big help in keeping rocks, tar and oil off the hulls. It also helps in loading and unloading. keep the wires away from the mast. Tied to or against the mast they grind/wear through the anodizing. Take them off if possible. Carpet line your sailbox. Put the heavy metal parts in the bottom. Then roll over that a layer of carpet. Now load in the next layer of parts. Keep metal parts and all hard parts away from each other. Use daggerboard and rudder covers. Put the sails in last, on top.
Do not carry your hulls/boat around on hard rubber rollers. I have seen sailors arrive at regattas only to find a hard rubber roller has crunched 2" up into their hull. Then they remember that big bump at the RR tracks they hit giong 60+ last night. These rollers do not provide sufficient bearing area or contact area with the hull. Long and wide carpeted pads do a nice job.
A mounted and inflated spare tire is a good idea too. Put a sum cover over it to make it last.
Have Fun,
Bill