i have a roller, same situation. my strategy is 2fold
i roll it down the jetbridge, but carry it on when i walk through the door
mine actually fits under the seat, so if the FA does say anything (which is rare since i'm holding it), i say, i've tried on regional jets and it fits just fine under my seat

there's actually i think more height under the seat than in the bins, so i've had 100% success rate with them letting me on.

i used to use that bags for overnight mileage runs and then i regretted it because it cause me to make connections i otherwise would have missed, and then could have gotten rerouted OAL (double miles), or nonstop back home with ORC.