Take the Challenger position and work on SWA at the same time. It could take several years to get on with SWA, and in the meantime the Challenger job sounds like it could be fun. How does your friend like the job/company/company principals? It's a lot easier going into a corporate job with inside info like that.

As far as the traveling, you can do a lot of traveling for the 30K difference in pay, if you just kept your standard of living the same. Split the difference in standard of living and you still have 15K to travel with.

Also, if the Challenger job does lots of RONs, join a hotel rewards program that gives points towards frequent flyer programs and be loyal to that hotel chain. It'll add up. I'm a Marriott Rewards member and it's been pretty good to me. I also have a Marriott Visa card that gives points for purchases and I use that card for EVERYTHING and pay the balance every month. I don't do much personal travel, but I've picked up some nice high-end merchandise (digital camera and a GPS), and several vacation hotel stays from that program. They usually have special offers on trips that include airfare and hotel stays. The points were earned at my company's expense, which they'd have to pay anyway. It takes a few years for your points in a program like that to build useful steam, but once it does you can really take advantage of it.