HockeyPuck - if the job sucks, but you love the Okanagan, then you've got a tough decision to make. Judging from what I'm understanding, if you made half of what you made now, you would still be able to live okay - you wouldn't be considering a move from the start otherwise.
Everyone in this thread tells you to stay in Calgary and build your nest egg with your oil and gas money here, which is good advice, but you should really also follow your heart. At the end of the day, on your deathbed long in the future, would you rather you died with good money and the straying thoughts of missed opportunities making you ask 'what if?', or okay money and completely satisfied you did everything you wanted to do?
You can move to Kelowna and still provide for your family too. Don't let anybody else tell you otherwise. Lots of families already live there doing that. You don't have to be a 1%'er to live there. Just make sure it's a job that you know can help you get somewhere else in the future too.
By the way, have you considered mobile independent consulting for your industry? Maybe that is a route you should consider. I'm sure there's a way to do that from Kelowna, at least on some level.
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