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Agree with D1. The airline credit card is a good idea - past that you go Hotwire, Priceline, etc. and book the best deal every time. Sooo much cheaper and often just as good since you can snag great deals. Even as a frequent work traveler, for personal I choose the best value (unless booking with points).
Once you start getting those free upgrades, paying a few extra bucks feels worth it
It depends. My family is on the other side of the world, and being a frequent traveler for SQ was worth it even before I was a consultant
I was executive platinum on AA (before the $ requirements came in) off 95% personal travel for a few years. Took some effort, and the occasional double EQM trip, but was totally doable.