I have a CSY 44 w/o with a double headsail
roller furling rig (Solent rig) and a boomed staysail. I also
single hand primarily. For my latest working
jib UK made a 100% fairly high clewed
jib. It sticks somewhat on the staysail
shroud when tacking but unless it’s really light air it does not need walking around. It’s a great sail from about 10-20kts. Anything less I use the big forward jib or
motor and anything more I may roll up the 100% a bit but primarily I depend on the staysail in heavy air. In 25kts or more she sails fine with just the staysail. I rarely sail her as a true cutter because at any angle off the
wind the staysail tends to blanket the 100% jib and does not help much with speed. A yankee would likely not be affected by the blanketing like that.
If my staysail was on a
furler I’m sure I would use it more but as it is it’s just more
work to raise, lower and flake.
These are heavy boats and need all the sail area they can get in light air. My boat is also a shoal
draft short rig so yours may differ. So my concern about the yankee would be the reduction in sail area and jib track sheeting angle. Your
sailmaker can help with that.
And finally, it also depends on the winds in the region where you sail and how you use the boat. Nothing wrong with your
current configuration. For the coastal and
Bahamas cruising I do my rig works well for me.