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It's all about getting the best for the least $. I believe there's nothing wrong with asking for a free upgrade (big tip if accommodated).
Enjoy playing the frequent flyer/stayer game. Used to travel full time for work, so I racked up tons of points & miles. Before that, my "get out of college" job was as a cruise ship musician. Sailed throughout the Caribbean. If my wife is reading this, honey, I had no fun at all!
Love to golf, ski, stay in the best locations. Favorite places include Lake Tahoe and Whistler for skiing, Mexico (Caribbean side) for great deals on beach trips. Golf in Nevada, Utah, Arizona, and Florida are favorites.
Always happy to help others with travel recommendations. It's a passion of mine.