Well, I would be lying if I said artstyle in general didn't effect how willing I am to pick up shows. Now obviously there are less superficial reasons for me to avoid something but when I have no idea of what to expect then at least appeasing my aesthetic senses can make the decision to start a series a little easier.
Now as far as comparing anachronistic character designs and current cast visuals. Well, I got into anime in 2006 and focused mainly on the shows the rest of the fandom was watching so I built an expectancy as to what a series should look like. It became pretty generic after a while though which is part of why I picked up Fist of the North Star and Legend of the Galactic Heroes. The artstyles of those two shows were refreshingly different but eventually the novelty wore off. Not that I jump into shows all the time for looking bright and shiny mind you.
On that note I don't find it accurate grouping character visuals from any single decade together solely for being contemporary.
Hidamari Sketch's artstyle is very different from
K-On!'s,
Yoshitoshi ABe's stuff has a look all its own from
Satoshi Kon's works, and
Ranma 1/2 has no aesthetic resemblance to
Fist of the North Star.