To trailer or ride to your destination.....that is most certainly a "personal" decision.
I trailer my bike the 5 hour trip to the rides in NC. I don't enjoy the ride on the interstate, or sitting in traffic jams in Knoxville when it is 90 degrees, and my bike is not really set up for hauling the camping gear. Most often I don't get to leave until after an evening meeting, and my drive begins at dark and continues until 2 AM. I much prefer to haul my bike on the trailer, my camping gear in the car, and spend the interstate time in my car with the AC on and the CD player going. Once I get to the riding area.....I will ride as many miles in a day as daylight will allow!
I have hauled bikes for thousands of miles, and I did learn that when you hit a really big bump, the bike suspension can compress and the strap hooks can come out of the eyelets/loops on the trailer. Some tie down straps have snaps or keepers that prevent this....but mine do not, and not all hooks are the same:
I have tried to find a way to make my hooks with keepers that would prevent them from dropping out....and for a while I just used masking tape to close off the open end, and I had to re-tape it every time I use the hooks. I think I have come up with a better fix. I cut a piece of rubber tube and slid it over the hook:
Then after you have attached the hook to the eyelet on the trailer - you just slip the rubber tube through the ring on the hook where the strap attaches.
Since I have started using these modified hooks......I no longer have to worry about the strap coming unhooked.