We had it real comfy and rode a midunit locomotive 🤪 with comfy seats, heating, floor space to sleep, windows that open, and even a kettle and outlet on the way back. To top it off I didn't take any days off and told my company I was sick so I could WFH on the way.

As for riding car, the old grain hoppers tend to be the best but they're fewer and farther between nowadays. Boxcars are almost always locked so your best bet is a car with a fully solid floor with some well space at the end, or an intermodal car where the box comes right up to the edge so you're not exposed to the tracks. A buddy of mine got lucky twice with an open freight full of mattresses one time, and a generator car that was spitting out some heat another time when it was cold.

Never ever hop onto any of these without someone experienced telling you it's viable.