Oh, I didn't see this before. I might try to incorporate some of this into my own when I get a chance!
Did not know about the Chase service rep, that does count for a lot! I've only ever called into the card services number on my Plat with Amex so maybe my experience has been different.
I agree on paper the CSP looks strong, especially in combination with the Freedom and Ink... 7% dividend, 5x on select categories.... what's interesting is that in addition to Freedom's $1500 quarterly cap, and the rotating categories end up dictating your behavior rather than fitting your actual spending patterns (unless you devote the time to gaming the system).
Adding an Ink Plus/Bold puts annual fees into or beyond Amex territory, and unless you can really max out that office category (which I assume entails some MS or again, gaming the system) it seems pretty hard to offset the additional $95.
Personally I try to assume a ~3 year+ relationship in which the issuers address easily exploited loopholes, and I don't blow time trying to micro-manage rules (which at almost anyone's "market rate" is probably a losing effort!)
Totally agree on the travel categories if you fly around for work a lot, although these days the flights are so expensive, getting 3x or 4x on those can be a lot more significant than dining and hotels. Might be very different for extended stays, I tend to make fairly short trips.
I have to create some pretty contrived scenarios where the Chase combos come out ahead, so maybe I'm just calculating things wrong?