Wellllll, I saw Lindsey 13 times on the UTS tour and 5 times on this tour. I wish that had been reversed though since I feel this tour outdoes the UTS tour major. Heh. I've seen Keith Urban, I think, 5 times in various cities. During the SYW tour, I saw Fleetwood Mac 5 times in England and 3 times in Texas. I went to Philadelphia twice to see Justin Guarini and went to Beaumont, Texas and Flint, Michigan to see him as well. There aren't many artists I do that with, just those few.
My feeling is...if you can afford it and your job allows it, go for it! I'm not married, no kids, I live and work at home, so I can travel around if I want. I am not planning any more trips until next summer, so I have to work my butt off until then to make back the money I've spent over the past few years. LOL
I was going to go on a couple of short trips later this month and next month, but have nixed those to help save money for a bigger trip next year.
No regrets.