The easiest and cheapest route to 500hp will be the 440 hands down.
But as far as a 440 ALWAYS outrunning a 383? No way. 383's can be had cheap which is appealing to poor people like me.

To many variables. Vehicle weight,gears, and the most important part to factor in is the overall engine combination. A well thought out 383 is very capable of taking down a 440 that's using a crappy selection of parts. I like both but I have a soft spot for the 383. A 383 with Indy heads can be down right nasty fast. Some disadvantages include lower torque and more expensive pistons. Block strength? 383 or 400 for the win hands down...

For a lighter vehicle, I'd have no problem with using a 383 at all.
A nicely tinkered 383 in an a body is too much fun but for the amount of headache and expense to swap in, I'd just go with a small block. Sometimes I like to build a smaller engine just to see what I can get out of it


Some people are stuck in the past. Newsflash!! Performance parts have come a very long way since the '70's. I am a nostalgia buff and I will gladly admit that. There are great cams,intakes and anything else you can think of being made now. Take the 340 vs. 360 debate for example. Stock for stock, the 340 WAS a better performance engine. Today the 360 will get the job done cheaper and better (again combination and YMMV factored in!) . I hear so many older people talk about how crappy the 360 is. Whatever. Just like the 440, more cubes and more torque equals the old saying "cubic inches or cubic dollars".
Yes, it's only 20 extra cubes but it makes a difference in the end.

I mean with today's parts you can make a 318 haul booty. Build what you have and never be afraid of learning something new. There is nothing like knowledge to make power