Turns out I have a continental ultra gatorskin for my front tire of my Trek. The rear is a "duraskin+K" continental. Should have put the gator on the back
My Lemond has a Specialized Mondo on the back. The specialized tire is a b*tch to get back on, so that might be a factor of the brand. I have to use my tire levers to get the last bit on, which I know can pinch the dang tube. But I can't just stretch it over like I can the continentals.
The Lemond needs both tires replaced to 23's because 25's are too wide to take the tires off without deflating them a bit. Don't ask other than the bike came with 25's. I've just been lazy about replacing them.
Thanks for the tips so far.
"Only the meek get pinched, the bold survive"