I still have my original warn winch on my 2007 machine. I have replaced the cable twice already, but I
also plow with it. I have taken it apart and cleaned it according to this guide probably 3 or 4 times. One time after cleaning it would not stay engaged. My dealer suggested to take part #14 in the attached diagram. (drive shaft) and shave off 1/16" inch from the end (towards the sun gear, #18) to allow it to go in a bit deeper and not strip out. There is still plenty of clearance for freespool mode.
One time I did strip these two parts, because I had the winch overloaded trying to pull a machine up a bad spot.
As for the starter question, it is easy to get to and remove. I posted links a while back on where to download the service manuals for free. The brushes in the starter were worn and I was able to find a replacement online for about $35.
Mike
Warn Winch diagram.pdf