I'm going to go the other way and say 500 HP should be a relatively easy target out of a nice 440 with decent heads etc., so I say don't stroke it. I know stroking motors is the current craze, but as I recall 440s back in the day, their longer stroke already had them at somewhat of a disadvantage to my high HP 383 which revved way quicker than they did. Not saying my 383 made more HP, but with a decent converter & rear gear I jumped into my power band a lot quicker than they did. So adding even more stroke would seem to me to make that worse unless you were going the high HP route with big cam, high compression and steep rear gear. I'll be interested to see what others say about this, I could be off base on my thinking.
Later, Jim