I have no experience with a factory issued Hi-Stall converter, but I can verify that the Dacco 764 Hi-stall replacement converter will flash to 2800 behind a mild 440.
If you're running stock heads, resist the urge to install a big cam or you'll very likely end up with a unresponsive slug that does nothing well.
Something along the lines of the Lunati Voodoo 60302 would be a good match for a mild 440.
We are running a custom ground Lunati cam with the Voodoo VH43 lobes and it is a torque monster in our 5200lb truck!
220/220@050 108+6 in our 440 w/ported 906 heads, RPM intake, 1-3/4 headers.
727, Dacco 764 converter, 3.54 Dana. Very fun combo to drive.