RE: Second plane...should I do it?
If the Cherokee is the plane that you really want, GET IT! You said that you wouldn't even put it together until June. I believe you wouldn't even sweat flying a new plane by then considering that you get ample stick time. If you are really concerned about it, get help with the first couple of flights with it until your in the comfort zone and enjoy it. Heck, I maidened a kit built Somethin Extra as my 2nd plane without worry. The Cherokee will be a great flyer for your fleet whether you decide fly it as a 2nd plane or not.