I owned a fin keelCatalina 22 and have experience with an American 23. I have no experience with the Windrose. The Catalina has a better quality build and is a more solid boat than the American in my opinion.
The windrose looks like a bigger boat for sure. Either is likely great for learning. A catalina will be eaiser to sell when the time comes. It seems to me the Windrose has a good rep though... If memory serves...never had one.