Great Lakes Sailor
Join Date: Jul 2001
Location: Saginaw, MI
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There are many answers to your question, but let me give you my opinion. This is not an uncommon scenario, and you will need to try some minor modifications of your tacking technique to see what works best.
When tacking, I do not release the original sheet until the sail just starts to backwind. On my boat, this is not only a more efficient tack, but it also lets the bulk of the sail pull the knot in the clew past the shrouds, and across the foredeck, and I do not begin trimming in the new sheet until the clew passes the mast. With small bowline knots at the clew, this is usually sufficient to allow the wind to pull the sale around, instead of the new sheet.
However, sometimes the "knots" at the clew get hung up on a baby fore stay. In that case, I usually have to wait for an additional second or so to let the clew pass the baby fore stay.
It also depends on the size of headsail, and location of your shrouds, since I have been on some boats where a little early tension on the new sheet will actually help the clew past the standing rigging., particularly with a large headsail (150% or more).
I suggest experimenting on the best time to haul in the new sheet, but try to allow the headsail to backwind just a little before releasing old sheet.
Also, try different knot sizes and types. You didn't say what type of boat, but some on this site prefer a hitch in a continuous line at the clew instead of the common way (my preference) of two bowlines (one for each side). Similarly, sometimes a rather long/loose bowline may pass the shrouds better than the small, short loop I try to tie.
Don't worry about the sheets damaging the standing rigging. Unless your rigging is already defective, the sheets are unlikely to "wear" on the stainless steel rigging significantly.
Hope this gives you some options to try. Have fun experimenting to see what works best on your boat.
Saginaw Bay, Michigan
"The pessimist complains about the wind; the optimist expects it to change; the realist adjusts the sails." - William Arthur Ward