I'll be honest - haven't read through everyone's responses so sorry if I repeat something.
First off, create a list of cities you'd ideally like to relocate. Make sure that they cover most of your interests and not just skating. Do you like brewing beer? Make sure there's a homebrew store. Like Coffee? Make sure there are some proper coffee joints. If you're single, scope out the scene on OKCupid or search forums.
Now, most importantly, once you've done this back research dig into the job market. See what's most lucrative for your profession. Some might be instantly crossed off the list. Not only do you want a job, you want the opportunity to grow/be head hunted.
Lastly, if you don't have a set profession then that second paragraph matters less. Just make sure the city has everything you think you want/need. If you've got the savings and are willing to grind it out - even if you are a professional - you'll find something. Personally, I tend to give myself 3 months if I like a city enough to stay there and search around for a full time gig. If you haven't found something after 3 months you're fucking up (assuming you're in a metropolitan city).
Just prepare yourself and go for it! It'll work itself out if you really want it.