Last year, I lost a full set of RE-01R's due to a combination of punctures and one massive bubble (due to a pothole, which also bent the crap out of the rim too).
Today, found a nail through one of my barely worn-set of Continental Extreme Contact DW's, right in the shoulder.

Who's had recent luck in filing claims against the state for damage to their wheels and/or tires? Is it worth it?

 

I've tried. The state will refuse to pay any damages unless they've had notice of the hazard and a "reasonable amount of time" to try to fix it.

I hit a big (like 12" x 24" x 4" deep) pothole an on onramp to I-80 one night. Instantly flattened the driver front and severely bubbled the driver rear tire. As I was pulled over and changing the front, a state trooper pulled up behind me so I reported the pothole to him and got his name as a reference. I submitted the claim and IDOT told me since they didn't have knowledge of the pothole or a chance to fix it, they weren't liable. Seems like crap to me, not sure if it would have been worth the time/effort to go through small claims court.