Personally I'd consider the following in a possible move:
- proximity to family: +1 for Calgary as the family lives there. As someone else mentioned if you're close to them a move would affect that
- recreation: +1 for Kelowna for having better weather, mild winters, etc. As a golfer I could be a bit biased here.
- income: +1 for Calgary for obvious reasons.
- lifestyle: depending on what you place the highest importance on this could go either way. Commute time, proximity to a major airport, location of closest NHL team, proximity to US border, etc - this one is all personal and could go either way
- cost of living: I don't know much about the cost of living in Kelowna but I'd expect it to be less than Calgary. I'd consider factors like gas prices, utility costs, property taxes, real estate, etc.
From the looks of it lots of people have considered a similar move either now or in the future. I've considered it too and I love the lifestyle there (mild winters, slower pace etc) but I like my job too much to leave it. I'd definitely look into moving there when I retire though (along with many others).
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