I've been Hilton Diamond for years. I'm also currently Priority Club Platinum and Marriott Silver. I'm also a President's Circle member of Hertz #1 Gold. I'm looking forward to losing all of that status, except Marriott, at the end of this year. I spent way too many nights on the road in my past life and way too many nights in OKC the first year of my current life.
As for gaining status, if you're a corporate/charter pilot, if you've got a trip with several nights in one place, you can bounce from hotel to hotel to get your stay count up and get the elite status quicker. Also, keep an eye out for promotions like stay X nights, get a free night. Last year, I did a 4 or 5 night stay in Orlando and got my base points, 4x bonus points (the promotion at the time), plus some extra points based on how my earnings profile was set up with Hilton and I got over 20K points in that one trip. I've also given my dad my Hilton number when he has gone on business trips (he doesn't go often, so he doesn't do the rewards programs) and I've gotten a bunch of points that way (and he's gotten the Hilton Diamond benefits).
I did a weekend trip to NYC with a stay at the Waldorf Astoria and round trip airfare paid for with points I've also done a weekend trip to Napa and had the whole trip (airline, rent car, and hotel) paid for with points, plus numerous nights here and there at random events.