Input on older Day Date

[TF7’s]

I’ve always thought of the day date as the quintessential Rolex, the yellow gold with the bark band is imo timeless. That being said I currently have a hulk and a Batman with the oyster bracelet. I don’t really need another watch, especially a newer model day date. Which brings me to the question at hand, are there some desirable older model 1990/2000 models that would be reasonably priced and desirable among fanciers. Any insight appreciated, thanks