looking for help up wind
Ahoy matey I agree with Jeff but here''s what you do. Lay flat on de cabin top as close to the mast as possible and while sailing take a picture of your mast under load on each tack.You ought to have some comprehension of the mast bend and mast rake and with both tacks photographed you should have a nice comparision. Second while sailing take a line weighted in the center say 10 pounds, foward , and drag back under yer boat to check if the board is down and how much line it takes to clear ought to tell you how far. Of course you''ll need some help for both of these tests and I firmly reccomend well endowed buck naked young women for this purpose. (distracts those pesky on lookers from your antics ).The board may retract and drop just fine out of the water but under load it my be jamming. If you have rudder concerns (Total area/depth) bolt a couple of pieces of plywood over it and see if it helps. As far as loose rigging there should not be any. If you can''t hear middle "C" you ain''t even close.
I suspect you have a trio of problems all adding up to the poor sailing you describe or possibly your snagged on the Edmond Fitgerald. Pirate of Pine Island.