I would change it. I put over 11,000 miles on my FST Classic and I replaced mine right in that area after they had failed. Ruined a trip to the UP. Don't wait for the failure, it's a matter of time now.
Adding a grease fitting now won't do much as most of the wear is done. They fail even when greased correctly, trust me. Polaris has made that bearing a sealed bearing and say they don't need greasing, but I'm no mechanic or expert, trust me on that too!