LME2011, congratulations,
Visit local marinas. In a couple of weekends, you should be able to track down an experienced female sailboat owner. Most sailboat owners are a gregarious lot and are more than happy to share their knowledge and experience.The problem for a novice female sailor is the the vast majority of guys have a John Paul Jones, "damn the torepedoes, full speed ahead" attitude whan it comes to the physical issues of sailing... in other words..."pull harder or get a bigger winch". Experienced womens sailors call to mind the old privateers where finesse was the order of the day.Solo sailing an O'day 23 that is properly rigged and maintained is well within the capability of even the most petit sailor...without any expensive add-ons.A couple of tricks on raising the main. I am writing as if you know very little for clarity...not because I assume such to be the case.As others have noted, the bow needs to be pointed directly into the wind. if the mainsheet and topping lift are slack, the boom will align on the centerline of the boat when you are pointed correctly.The track/slot on the mast and slugs/luff rope on the sail need to be clean and free of crud and corrosion. Get a can of SailKote lubricant. It makes boat stuff slide like a miracle and won't harm the fabric or collect dirt.If it is still a bit hard to get the main tight after this and you don't have a winch for the main halyard...bowstring. When the main is up, or mostly so, loop the halyard a half turn around the cleat, hold that end in your weaker hand, put one foot on the mast and pull the halyard away from the mast like a bow string with your stronger hand instead of trying to pull it downward. As you release the tension on the pulled out halyard, pull up on the cleat end with the other hand. Repeat the process until you are satisfied with the luff tension of the sail.This is the way I learned to raise the big, heavy, canvas, gaff-rigged sails on the winchless old wooden boats that I learned to sail on as a youth. Even a small person has a great deal more leverage pulling outward than a large person has pulling down with mere weight.