So I bought a brand new Cannondale CAAD8 about 2 months ago and have put just under 400 miles on it in that time. I'm brand new to road biking, so I feel like I still have a lot to learn. The first 150 miles I never got any flat tires at all, and everyone just kept saying that they were inevitable. When I finally got a flat, I did some research and was able to replace the tube pretty easily. Since then, I've gotten 5 more flats in about the last 200 miles. I ride 15-20 miles a day, and I'm starting to feel like a day without a flat is a wonderful occurrence instead of the norm.

Every flat I've gotten has been on my back tire. When I've bothered to find the hole, they always look pretty similar to this picture: http://i.imgur.com/pwEF4kh.jpg

I haven't been able to nail down whether it is in the same spot inside my wheel or not, but every time I get a flat I run my hand through the inside of the wheel and I can never find any debris. I checked the tape on the inside of the wheel and it seems smooth and in tact as well. I make sure to not use my tire levers when putting the tire back in place, and before inflating the tube I double check that the tire itself is fully on the wheel without pinching the tube anywhere. The only thing I can think is that I simply have really shitty luck.

Can anyone think of something else I can try? Would replacing my tire with some Gator Skins help? Is it normal for most/all flats to be on the back tire while the front is completely fine?

Edit copied from a comment: So after posting this, I dug around for all my flats and found 5 of them. I took the only handy tape I had, electric, and tapes each of the holes so I could check if they're in similar locations.

http://i.imgur.com/QUR7uJp.jpg Shit.

Feeling like I should have done that a while ago, I started looking for the culprit. I haven't been paying attention to keeping the tire in the same position everytime so my first thought was it had to be on the wheel or wheel tape. I checked the whole thing, especially in the location the punctures were, but didn't find anything. I even took a wet rag and ran it along the wheel tape but didn't really notice anything come off. Finally, I grabbed the wheel itself and took a look. at first glance it seemed fine, but then I noticed something that should have probably been obvious a while ago:

http://i.imgur.com/9xijX1i.jpg

I'm assuming I stretched it out with my tire levers at some point and its been wearing thin ever since? Does this look like it would cause the punctures I've gotten?

So the obvious solution (assuming what I found is the problem) is new tires. Ok. So back to GatorSkins. Worth the money?