you won't want to do to much back and forth when re-spooling the winch line, synth line should be put back messy, if its all neat and tidy on the drum next time it is under tension the line will tighten on the drum and the friction will damage the rope. just something to think about. also if you look at a comp style winch i'm pretty sure they run a deep narrow drum so you might be able to get away with your initial thought of putting something around the hole to act like a fairlead, just make sure its strong because there will be alot of force applied to it when the winch is in use. hope this helps you out a bit.
oh and cool looking front bar. :rock: