Hey Airguy,
You might want to find my posts about the flying chain guard (Misc section) and my latest posts about chain wear (performance mods section) replacement.
From recent experience a new tire runs about $160, not including mounting (not including labor), new chain guard runs about $80 with bolts and tax. Fender dings will go unrepaired. New DID 525 ZVM X-Ring chain $141.00 (replaced it myself).
Why do I know this stuff? Because I failed to adjust the OEM chain often enough (even though DID 525 VM is an O-Ring Chain) it just didn't hold up well after it became way to loose and came off the rear sprocket at 65 MPH eating the chain gaurd which flew off chewing up the rear tire in a heartbeat of time. Sure I put the chain back on and adjusted it to normal tightness. Within weeks it was very sloppy loose again (no axle didn't move) so I adjusted it again. Within another two weeks it was extra sloppy loose. At which time I did some research on chain failure (see links in the two posts mentioned). Chain stretch and sluffing off oxidation (even though I cleaned/lubed often) were all tell tale signs of failure. Oh and by the way if you have an O-Ring chain on your bike and you don't see ANY O-rings, that is not a good sign either (that was also my problem). Bottom line keep the chain properly adjusted and lubed (yes you have to lube O and X Ring Chains) with a quality lube. I USE to use Maxima Chain Wax, but never again. I'm going with the #1 Rated Chain lube PJ1 from now on.

Steve
Learning from my bad mistakes, over and over again, so you don't have to.


bigsteve