Agree with Tom S .....
Sloops are simpler. Fractional Sloops (with max. mast height UNDER 60 ft so you can clear most large bridges) are even better as all you have to do reef the main ... or sail on main ONLY. A fractional sloop with a removable spinnaker furler/foil will remove the disadvantages of the fractional sloop for down-wind sailing .... just furl the A-spinn when not needed. True Cutters are for close to broad reaching (trade-wind sailing) and are poorer for beating and dead-downwind running. Plus cutters are usually HEAVY boats that require a LOT of sail area to keep them moving at speed. I have a 'heavy' cutter and my choice was dependent on the WEIGHT of the largest sail that I might have to manhandle someday on a wet pitching deck .... a SAFETY consideration. BTW a healthy individual probably cant manhandle more than a 400 sq. ft. sail on deck when the seas/winds get 'boisterous'. A cutter is 'versatile' but to make it really versatile one needs a forestay (the stay that staysail flys on a cutter) to be removable, as tacking a cutter constantly is a BIG PITA. A true cutter has the mast at approx. 40-50% of the LOA (Robt. Perry or Bill Crealock designs are close to 'true' cutters) and the CE is in FRONT of the mast and are sailed 'differently' than sloops. Double headed 'sloops' are still sloops and are sailed like a sloop ... Island Packets, etc. Ketches, etc. simply have too many sails to work and need larger crews ... and when going upwind only the headsails are the ones that are 'working' .... the 'aft' sails just sitting there in the turbulance/windshadow of the foresails. For 'ease' especially for 'coastal' that requires a lot a beating .... go with the simplicity of a (fractional) sloop.
Sloops are simpler. Fractional Sloops (with max. mast height UNDER 60 ft so you can clear most large bridges) are even better as all you have to do reef the main ... or sail on main ONLY. A fractional sloop with a removable spinnaker furler/foil will remove the disadvantages of the fractional sloop for down-wind sailing .... just furl the A-spinn when not needed. True Cutters are for close to broad reaching (trade-wind sailing) and are poorer for beating and dead-downwind running. Plus cutters are usually HEAVY boats that require a LOT of sail area to keep them moving at speed. I have a 'heavy' cutter and my choice was dependent on the WEIGHT of the largest sail that I might have to manhandle someday on a wet pitching deck .... a SAFETY consideration. BTW a healthy individual probably cant manhandle more than a 400 sq. ft. sail on deck when the seas/winds get 'boisterous'. A cutter is 'versatile' but to make it really versatile one needs a forestay (the stay that staysail flys on a cutter) to be removable, as tacking a cutter constantly is a BIG PITA. A true cutter has the mast at approx. 40-50% of the LOA (Robt. Perry or Bill Crealock designs are close to 'true' cutters) and the CE is in FRONT of the mast and are sailed 'differently' than sloops. Double headed 'sloops' are still sloops and are sailed like a sloop ... Island Packets, etc. Ketches, etc. simply have too many sails to work and need larger crews ... and when going upwind only the headsails are the ones that are 'working' .... the 'aft' sails just sitting there in the turbulance/windshadow of the foresails. For 'ease' especially for 'coastal' that requires a lot a beating .... go with the simplicity of a (fractional) sloop.