Tim, Calgary is certainly not Houston, but it's more American than most of Canada. And Jeff Mingay overlooked lots of good golf in Calgary, although the season is short (May through September - lots of sun June July and August). Clubs close early October, regardless of the weather. April can be nice, or not.
1. Negotiate with your oil company for a golf club membership - there are some good private clubs, if they pay.
2. Public golf is OK but very busy, t-times are crazy at all of the better courses. However, with planning there are times available in the nearby mountain courses.
3. If you have family, they will like Calgary, as long as they can be driven places. If you like hiking, biking etc - Calgary is Superb.
4. Taxes are OK, bring your car from the US. Traffic is weird, so many roads all set up like a giant Snakes and Ladders game.
5. Medical services are outstanding, even better with your corporate plan.
6. Are you Canadian or US citizen?
I'm a "retired" golf pro, living in Calgary (Okoroks is just south of city) because we have two sons and their families living here, and my wife doesn't want to be anywhere else as long as we have grand children! Most of the players at our course (D'Arcy Ranch) are in the oil business, in fact most people with money here are in the oil business, or hockey players. D'Arcy was designed and built by Texans.
Email me anytime, or call me. cheers