Here's an interesting article on how to get a free upgrade, not just with hotels, but also with airlines and car rental agencies. I know there has been much discussion on here about being entitled to free upgrades, and this article assumes no such thing. Still I was enlightened by some of these tips, especially with regards to hotel upgrades. Read on.
I agree with the rental car strategy. For years I have been Hertz Gold and have never booked anything more than the cheapest price car. I get there early. I always drive out with the full size or SUV. Only one time can I remember getting what I booked....and that was a few months ago in Boston (nobody rents cars in Boston in the winter). But, it didn't bother me because I got 40 miles to the gallon in the car I got!
Other than the rental car gambit (which is as old as dirt, and simply an understanding of basic supply and demand), most of those "suggestions" in the article are mostly rumor, vaguely anecdotal, and pretty unreliable. No mainline US air carrier gives FA's upgrade authority that I'm aware of, for example, and the other suggestions are patently laughable. I don't even take a little box of chocolates to the counter agents anymore, that one quit working about eight years ago (but since I check in online at precisely 24 hours in advance, I bypass the counter anyway).
The "trick", if there is one, is a combination of rate or fare paid, status, and timing the flight or stay to ensure the least competition. Other than that, I'm afraid, is mostly wishful thinking. Being #32 on the upgrade list when there's one seat open, well, it ain't happening, I don't care what you wear, what your story is, or when you show up.
I agree....and that's why I only referenced the car rental matter. I've been doing it for years and learned it about 45 years ago on a trip to Florida when I booked a low priced car, they didn't have it and I drove out in a Cadillac for the same amount of money as the economy car I rented.
That little light bulb went off in my head and I've done it that way ever since.
If you're not upgraded on the airlines before you print the boarding pass.....there is no upgrade.