Personally I really like my 6.1L hemi and would not think twice about swapping one in if I were in a position to do so. The heads flow 300 cfm on the intake side without any porting! Stock they churn out 425 hp. A "couple" of bolt ons (good exhaust, intake, tuner, etc.) you can get upwards of 400 whp and 400 wtq out of them. If you go the carb route, may be able to "tune it" even easier. I would go 6.1 or 440. Not the 5.7 as it has MDS and the '09 up have VVT and not sure how you would control that if you stayed with a carb set-up. But the '09 up 5.7 heads are said to be even better than the 6.1L heads.

A decently tuned 6.1L with bolt ons will DEFINITELY keep up with a "mild" 440, but a stroker is another story. My buddy with a "stock long block" 6.1L SRT8 charger running E85 has hit a best of 11.85 in his car on slicks, lightening the car up some (no rear seat, carbon fiber trunk lid, etc.), Cold air intake, torque converter and a 90mm throttle body. Good luck!