I'm also in Upstate NY, and have done plenty of mowing in what looks like similar conditions to your pics. I've got a ck3510se, with a 2060 cutter. I banged the blades up pretty good last year, so they're far from sharp, but it's still doing a fine job this year cutting.
Like others have already said, your primary culprits are likely: going to fast, and not having the rear of the mower set high enough.
When mowing the really tall and thick stuff, I put it in low range, and keep it to a snails pace. It's faster to do it once slowly, than having to do it twice.
Here's a picture of my cutter from last year (when it was still shiny and new). This is the rear height setting I keep it at. I generally mow in 2 positions depending on which fields I'm mowing. Either the front end riding on the ground, for the lowest possible cut, or raised up about 3-4" for a 6-7" cut.
View attachment 613441
Thanks. That's actually lower than mine is currently set. I think the main issue here was a field that had a few years of no attention and weeds that were taking over. I went back over the top, flat area after a couple days and it looked great. Running a bit slower on the hill helped make a single pass look acceptable.