[RThig]

The Windsor has a taller deck height than the Cleveland (9.5" vs. 9.2") so it's easier to package a stroker kit and you can go bigger on the Windsor. Canted valve heads are a better design, especially the newer aftermarket versions. The hot setup for the last Engine Masters Challenge was the "Clevor" with a Windsor style shortblock and the CHI Cleveland style heads.

I believe the main reason you see more Windors is that they had a longer production run and there's just more of them out there. The fact that they share a few pieces with the small blocks also helps with the aftermarket parts availability.

I think either engine looks great in a Cobra and infinitely better that any brand X motor!