Feel like my 440 should be faster

IMHO, probably a toss up between changing the gears (not street driven I guess) and having the cam reground for your combo (just less duration for lower ivc for more dynamic comp for the 9.38:1 static comp), then swap to the old converter which should stall higher than the 360 with the 440 but less than 2500 and get some of that around town, low end torque back and lower trans temps.