This is Moparts. Budgets don't count, we don't care. You must install the parts we choose because this shall become
our fantasy project, not yours!
And if that 440 is even the slightest bit tired, a stroker crank and alum heads will be debated next, quickly followed by a 440Source hijack debate.
Joking aside, don't worry too much about running logs on a mild 440 - they aren't ideal, but you can still have a strong runner if the 440 is in good health.
As mentioned already, if you have an H-pipe setup, better plan on cutting the H when going from 383 to 440. You can probably reseal it with a $13 bandclamp afterward, though.