Good points.
I also feel like the remakes are making some hesitant to cough up the bucks for classic WPC A-listers, and perhaps the rarity of the B-listers (that most likely won't be remade) is boosting the prices. As somebody that has a TOM (rumored) and a MB (LOL), I'm certainly weary of picking up any A-list 90's stuff now.
And yes, it's happening rather quickly: I've only been in three years and change. One of my first pickups was a really nice WH20 w/ perfect topper for $3700. Seems like 5k gets you a decent playing beater now.
I dunno, I just dropped $4500 on a perfect HUO BK2000 so I don't know what the hell my buying habbits are anymore haha.
Safest bet for me lately is picking up HUO Sterns that have been out for 1-2 years, and will probably continue along that path for the most part.