You can get 400 to 500 HP out of a 1 liter fuel injected supercharged motor so what difference does it make
Shoot, last show I was at they had a turbo saturn motor making over 1000 hp... no juice. Pick what makes sense for you. Either can make that much HP without efi or supercharging... and efi systems don't have the edge like they used to... so long as max hp is a concern. Me, I like the cleveland. Aside from the good stock heads, a stock bottom end that will live all day at 7000rpm (pro stockers ran 10,000 with 'stock' crank and never broke them) with nothing but decent pistons, bolts and assembly, they also make a number of great heads for it. Everything from the 'I only read the Jegs catalog' Edelbrock heads to CHI, AFR, the 2V and 3V, even a four valve per cylinder double over head cam set (bring a BIG check book). The canted valve design has the leg up. Look at many V8 ford racing engines.
BUT, both make a great motor and at the power levels you are talking, either can do it in their sleep. I give the nod to the Windsor in the $/HP game, I give the cleveland the nod in the designed to run game... short lived as it may have been in the states. I also kind of like the ease in making a 427 windsor... give them a wink and a nod when they ask "Is it a 427?"
Lets see, Carroll put a 260, 289, 390, 427 side/center/low/medium/you name it, 428... in them so pick a motor and enjoy the ride!
Me, I would just pick what makes sense to me. Mine came with a cleveland so that makes sense
Just to through a wrench in it, a great motor today is a clevor.
This conversation is a lot like the bb vs sb or ford vs chevy... run what makes sense for what you are looking for