Guys, I swear i'm not really the incompetent moron I appear to be. Travel booking is just the Universe's way of trying to break me for some reason. I'm mostly blessed so this is what they came up with.
It was not a SW trip, I can almost always figure that out. After thinking about it more, 45 min was just not enough time so I called Chase and spoke to the nice lady again. She was like, yeah, agree with the nice Delta lady, you should have never booked that even though it was a choice on both of our websites. Since I already had a separate return flight with a different airline (again, not many options from KC), I just asked the nice lady to book another flight that I found that left way earlier, but had a longer layover. While trying to cancel this flight she said she couldn't and that I was not in my 24 hour window. I politely disagreed and told her I was looking at my confirmation email with a time stamp saying I had like 4 more hours. After a while she got it cancelled,

I had already had the American site up (that was my return flight originally) and I told her what to book. She found it and booked it so we were ready to go right....right.... Well Mrs SF was next to me trying to keep me from smashing everything and cancelling the family vacation altogether and she quietly tapped me and pointed at the American screen I had up. The exact same flights were over $500 cheaper in total on the American site than through Chase. Now, Mrs SF knew at this point that bringing this up might make me explode because I was almost finished with this nightmare, but $500 is $500. I mentioned this to the nice lady at Chase and she just said that happens sometimes.(of course it happens to me right?). So after all that, I asked the nice Chase lady to go ahead and just cancel the whole rough ridin' thing now and I thanked her for her time and Mrs SF reentered all the crap on the American site and we are booked.
Thanks for listening everyone. I'll post here again yelling about travel people if my trip this weekend to see the Cats play on the beach gets messed up.
Go Cats