I can point to two examples-
I saw U2 ten times on their 2005 tour- although, to be fair, six of those shows took place five miles from my apartment. Along the way, I turned the trip to San Diego for opening night into a long (Easter) weekend, with a couple days in Vegas beforehand, and had a blast discovering one of the most underrated cities in the country, Pittsburgh.
As for Fleetwood Mac, I saw them seven times on the SYW tour- only twice in the city I lived in. Again, I made the effort to travel to opening night in Columbus (front row center tickets helped), and enjoyed traveling to cities such as Nashville and Madison.
To me, what really made it worthwhile was to make it an excuse to spend time in cities that I either already loved or hadn't been to before, but had an interest in exploring. It's also a big thing for me to go to opening night- due to the anticipation and everything involved in the show & the tour, etc.
If you have the money & the inclination, go for it! Just make sure you're racking up the frequent flyer miles
