You know, you're right that they are dated and would be unusual today. I say go for it!
I'd choose
Lindsay, because I know and love one. Plus I happened to grow up with three Ashleys, neither of which I really liked. But both names have the same vibe otherwise.
Meadow Lindsay is very nice.
Willow Ashley is okay, but I don't like the Willow-Ash thing together, it's too tree-y. :)