Cutter to sloop
I must say that I also agree with twilk that all too often I see comments from people who have never really owned a cutter, or had sufficient time on cutters and other alternative rigs to intelligently make an informed decision voicing an opinion in these discussions. I frequently see the ''common wisdom'' about cutters quoted by people who have not sailed on enough boats with different rigs to understand a cutter rig''s very real liabilities.
Having owned a cutter for 11 years, sailed on and off on my father''s cutter for close to another 10 years, and after spending countless hours out on the water coaching people on how to get better performance and easier tacking out of their cutters, I still think that cutters are an obsolete, pain the butt rig, especially when used in concert with a Genoa jib. I am not alone here, even such notable designer of cutters rigs, Bob Perry and Ron Holland have descibed cutters as an obsolete rig and a pain in the butt.
At its best, the cutter rig only makes sense on fairly large boats (something approaching 40 or more feet in length), where the slot can be large enough to permit a decent air flow and cutters only make sense only in a sailing venue where there is adequate winds to provide adequate drive without resorting to a Genoa.
There is this whole mythology about de-mountable forestays and the utility of a staysail as a storm sail in a blow, but having tried to rig these on a decent sized boats in a reasonable breeze, I don''t see how anyone can think that a removable forestay is even remotely a good idea. Few cutters really do balance under just the forestaysail and single reefed mainsail and in conditions where a double reef is warranted most forestaysails are too light a fabric to be of much use.
I also agree with twilk that you should avoid the windbags and make your own informed decision. I agree also that if you want to make an informed decision, go out and sail on cutters but also on more modern, easier to handle rigs in a wide range of conditions. It will probably sour your taste for a cutter but if it doesn''t, at least you will have a sense of why it doesn''t.