Let's deal with the headsail just for fun. I'm not going to get into
halyard tension for different winds because typically cruisers adjust it when they put the sail up and it stays that way until the sail is removed. I'm also not going to deal with backstay tension to tighten up the forestay because again most cruisers don't use these controls. So that leaves the position of the fair lead and this is very important. Make sure your sail has a set of tell tails positioned about a foot back from the luff. Now sail the boat on a close hauled course with the tell tails on both sides of the sail streaming back. Paying careful attention to the telltales start turning the boat into the
wind, this will cause the inner tell tails to break, if the upper tell tail breaks first move the fair lead forward, if the bottom breaks first move it back. It might take you a couple of times but when you finally nail it and the tell tails all break together when you pinch up into the wind make note of the fair leads position, for example 8 holes from the back of the track. For a cruiser that's good enough and you can reset the fairlead in the same position every time you expect to be close hauled or beating. When on this point of sail keep both the forward and backside tell tails streaming, if the inside telltail is lifting steer a bit more off the wind until it's streaming. If the outside telltails are lifting steer closer to the wind until they are streaming.
Now as you bear off the wind and esse the sheet your fairlead is going to be moved forward , this stops the sail from twisting off on the upper part of the sail. You will get to a point when the you ease the sail and you can no longer keep all the tell tails flying so don't let that concern you simply ensure that the top part of the sail isn't luffing and you'll be close enough. When you're really off the wind it makes sense to pole the
jib out. Generally the further you are off the wind the further out you should move the fairlead . I use a snatchblock set into the toe rail to accomplish this. When you get the fairlead positions properly set for close reaching and beam reaching, again, mark the number of holes and you can come back to these positions. Even if your not exact you're
sails will be set and trimmed better than most cruisers. If you like you can apply a second set of tell tails at your first roller reef point, make sure you mark the bottom of the sail, the foot, with sticky tape so you can come back to this position when you decide to reef. You can go thru the whole excersize again marking fairlead positions. The most important thing to know is always move the fairlead forward when roller reefing or your sail will be twisted right off at the top which will deposed the sail. That gets to depowering sails, move the car back, it will cause the upper part of the sail to twist off and depower it. It's really good to have fair leads that you can adjust while the sail is powered up, they will have pulleys on both sides of the fairlead that allows you to move the car back and forth with the sail fully powered. Many cruisers don't have these and that often means they don't properly trim sails because other than the lightest winds even if you ease the
sheets it's very hard to adjust the fair leads. What I do is to put a rolling hitch with a separate line attached to the toe rail or anything that is solid and nearby on the headsail sheet slightly forward of the fairlead and then ease the sheet until the second line is taking the load and then you can easily move the fairlead. Once the fairlead is in the new position you
winch the sheet tight which removes all the pressure on the rolling hitch and you then simply remove it.
Ok that should give you something to go and play with, if you want to pm me I'll tell you how to properly set and trim your
mainsail. Cheers, R