I have an Offshore 38 cutter that I have only sailed a couple of times and without the staysail. It had a strong weather helm when the wind blew from 60 degrees off the bow, but won't point unless the the rudder in cranked all the way to keep the bow up. But then the boat loses speed and blows off.
The man who built and sailed it for years says the staysail balances it well, and I can see that that would compensate for the weather helm, but I can't easily see that a staysail would help it point.
Does anyone know why a staysail might help it point? Or have any other ideas about sailing into the wind with Roberts Offshore 38 cutter? Thanks.
I'm not entirely clear on the behavior of the boat. You say it has "strong weather helm" which means that it wants to round up to weather, and then you say you have to "crank the rudder all the way to keep the bow up" which would indicate that the boat has severe LEE helm not weather helm.
Lee helm occurs when the sail plan center of effort is too far forward of the keel, in which case more headsail is going to make it worse. Weather helm is the opposite; too much power aft making her round up, in which case more headsail might help.
Any time you have to use more than a few degrees of helm just to keep a boat going straight you have a poorly balanced sailplan. If you have to "crank" the helm over to keep it going straight you have a severe imbalance. As Faster suggests, it is likely that your mast rake is wrong. If the problem has always been there as the PO implies with his tips, then you could be dealing with an incorrectly positioned mast.
You need to clarify whether you have weather helm or lee helm, and what sails you are flying when you have the problem.