Definitely wear them in before lubing, otherwise they'll always be just a little bit scratchy.
I don't know the actual figures, but on my main driver there's now a big difference between the well used keys like E and T and the less used, like Tab and Win. I've been using it with the current Clears for about 9 months. Really don't know how many presses that equates to, but I'd like to make a machine to do it for me for my next board. I don't like the inconsistency, especially when the well used keys feel SO good and the lesser used are SO scratchy.
Worn in ErgoClears are amazing.