I have heard it argued that the 3" main journals on the windsor limits the rpm, due to the surface speed on the larger journal shear thining the
oil. In theory that has to be true.
If you are going stroker, you do not need all those rpms anyway.
If you stroke the cleveland, you will not need the rpm either, and the oiling system is good to 6000 or so as is.
IMO the cleveland was the superior engine when they left the factory, but over the last 40 years more parts and building techniques were developed for the windsor. The bigger windsor block can be stroked to more cid.
I have to agree the cleavor is the ultimate big small block.