JK,
I think that the main difference in the Cleveland and the Windsor is the cleveland has a shorter deck height at 9.2" as opposed to the Windsor's 9.5". This allows for a longer stroke and more displacement on the Windsor. Most people won't push the Cleveland past a 408 or 418 CI. I've seen Windsor's stroked to 460 CI before. (Hall's Purple Passion)
Also, the Windsor seems to be much more available in parts and in crate form.
Steve
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