I like the 442. I had a chance to buy one for $6500 in 1985-86. I was 16 years old, that was a lot of money and there was no way to come up with it. It was a W30 455/automatic car. The owner went and got it out of storage took me for a ride in it. What a beast.
Cleveland and Windsor are both small blocks. But the Cleveland will look physically bigger. Clevelands have 2.75" main bearing bores, the Windsor 3". Clevelands used canted valve heads, while the Windsor used inline valves. The Cleveland begged for RPM, while a Windsor made torque. There are other differences, but I think this is what you were looking for.