I think it's all about finding what you can do, the cheapest you can do it.
For example, i target weekend shows so i don't have to take anytime off. I know Let has options for switching shifts with people so she doesn't have to put in for PTO. If there is a show during the week i want to see, i alter my schedule by coming in early, working late the previous night, etc.
Most of the shows i've seen, have been within driving distance. Anything 6 hours or under can be done in one day if i have someone with me which makes things a lot easier. If travelling to see a show, it's been to locate the nearest NESSAholic and stay with them, save costs of hotels and such.
Ultimately, it's about spending what money you will have to when travelling the best way possible. Couple shows i've been to were combined with vacation trips, like when i went to Vegas and to the UK shows, i planned my existing travel around when VC would be there and hit up the shows i wanted to see. The key is to find runs of several shows in a row, over a holiday weekend in your area! That way you can go to 2, 3, or 4 shows in a Row, not really take any time off, and just kinda follow the bus
Does that help to answer any questions? :-P
-katia