Hello, I have trailered my O'Day 26 several times, as far as 90 miles one way. I leave rigging attached save the headstay, bind it up of course and lie the mast on the rails front to back I take some of that pipe insulation and wrap it on the rails first and duck tape the ends then lie the mast on the rails to protect the mast and rails from rubbing. Then I use shrink wrap, buy at home depot or office max wherever, small hand help roll, and wrap halyards and stays to mast to secure. Duck tape tends to leave gummy residue on the halyards and cables.Then I tie the ends of the mast to the rails with rope and or bungees, and shrink wrap..
Once done, to truly secure mast I then use ratchet straps to hold the mast down to the deck. In the middle of the mast where it meets the cabin top I use cushions to support to prevent bending and bounce, and secure that with shrink wrap as well.
This method worked for my previous boat for seven years and seems to work well with the O'Day 26. Only other suggestion would be to tape any lose turnbuckles. I have lost them for some odd reason, I suppose it's the vibrations from travel they unscrew themselves and fall off. I have arrived at the lake to launch only to discover I was missing one or two! Not a good day when that happens.
When I bought the boat, I contracted a hauler for the first move, and he simply strapped the mast to the rails and hauled. Boat arrived in good order. He did not do the overkill with shrink wrap and bungees he simply tied the mast to the rails and off he went for 250 miles! He did not seem concerned and was a good hauler and very professional. I felt confident in his method, so I duplicate it for the most part when I haul myself now.
Hope some of this helps. Good luck with the haul.