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Seems like it's improving. I hadn't thought that the number of brands not depreciating were so small.
Airhead-
I'm generalising a lot… you can definitely pick up a lot of GSs cheap especially in the US on forums and private sales. But nearly all brands are going to depreciate to a greater or lesser extent, barring a handful of rare references. And even the universal Rolex bulletproofness is really quite recent and probably won't last forever.
They're things to be worn and enjoyed at the end of the day.
Regal
Was it ever? Only Rolex and PP and a small number of AP references are depreciation-proof. What about all the other brands?
I think in the US, GS prices have always been lower. Dealers give bigger discounts than in Europe and second hand prices have definitely been lower especially for quartz pieces but I think that's changed a bit. Limited edition Grand Seikos that are in demand definitely appreciate. Eg the "Whirlpool" is at least 50% over list these days, as is the "Peacock" GMT, and the Ryusendo to name a few.
Vintage prices for the best pieces have also kicked up.