Interesting question Sam. I may be looking at this all wrong but I would have to say the travel part of this would be extremely difficult. I know that USAC teams do some traveling but much of the racing is located in the midwest. WOO travels from coast to coast multiple times during the season including up into Canada. Being on the road consistantly has to be a drag. You better like the people that you are traveling with for sure.
Just a few of their trips include Perris, CA to El Paso TX to Paducah, KY in 6 days; Dodge City, KS to Lima, OH in 4 days and Ohsweken, ONT to Pevely, MO in 3 days.

Working on the race car on the road has to be difficult and also the hauler needs maintenance on the road as well.
This to me would give the nod to the WOO teams. Racing wise, you better bring your "A" game every night to both series. Probably not the answer you were looking for.