Your main winds up into the mast on a 250? Didn't know Catalina was doing that on the smaller boats.
I used to have an older 25, and I hated the way the boom had to be clipped to the back stay before I could lower and flake the main. Of course, to do so I had to point directly into the wind, clip the boom to the back stay, then race forward to douse the main before the wind shifted!
I installed a topping lift to eliminate this problem. A topping lift is a line from the masthead to the boom, and is controlled thru the use of a halyard. With a topping lift you can drop the main without having to point into the wind, and you can even drop it on a run if you wanted to, without the boom crashing into the cockpit.
Look up "topping lift" at Catalina Direct or West Marine to see what is involved.