I rode it North to South to North in 2014. Definitely hillier on the north end. They tend to be longish grades, not so steep. There are mile markers most or all of the way. In the hilly bits, I decided the uphill miles were long and the downhill miles were short - that was a pretty successful mind game.

One memorable moment was around dusk on the return. I was following another cyclist by 1/8 mile or so, just enough I could make him out in the fading light. I saw a coyote trot out into the road behind him, stop, lift his nose and sniff the air. When it heard me coming, it trotted away. I wonder what fresh randonneur smells like to a coyote. Makes me wonder what's going on behind me.

Trace miles are about the most stress-free road miles I've ever ridden. I think I clipped in at the start, turned on to the trace, and didn't make a turn or unclip a pedal until I needed water 60 miles later. No navigation, no thinking, the miles just tick by.

I can't help too much on hotels. I'm sure you know the Trace is a limited access road with little services. Small towns are generally just a bit off the trace.

I recall there are two segments with traffic to be concerned about - Jackson, MS is one, and frankly I forgot the other. Fortunately the traffic is concentrated at rush hour, so you might get lucky with your timing. If not, I strongly suggest pulling off somewhere and waiting a couple hours.

I found it delightful, and would like to ride it again. This time I'd stop and see some of the history, rather than riding it randonneuring style.