I will definitely repack the bearings as it's been ~1yr since the last time, and I do have bearing buddies. And I have one spare tire.
If you repacked the bearings only a year ago, pull off the dust caps and check the grease. If it's mocha colored (water), then repack. Otherwise, you should be good to go.
As for the tie down, I've created what I think (?) is the preferred system. I tied a short piece of 5/8" rope with bowlines on each end that attach to each cornet post. They are long enough for the lower knot to just drape over the inside edge of the hull topsides, and then I connect those with ratcheting tiedowns to oversize eye screws mounted firmly to the trailer cross bars. It seems very solid and I haven't had any issues, yet.
Almost the perfect system - go around the sidebars and over top of the corner castings with your rope, instead of going around the pylons. The object is to have nothing touching the fiberglass.
Chafe is your worst enemy on long trips. A fluttering strap or cover can wear through fiberglass over a 700 mile trip. If your straps flutter, put a full twist in them before hooking them up.
The boat will get dirty on the road. Especially if it rains. I use a cover for my mast, but only because it's a pain to clean properly, and I can leave the rigging on without it getting dirty.