!) Low friction sail track makes raising the main much easier. I have one made by Tides Marine. Dutchman makes a similar product.

2) The Dutchman answer to your lazy jacks would make stacking the main easier but I don't care for the drawbacks. You would have to use a permanent topping lift and if you have any roach on the main, IMO it would cause a lot of chafe.

3) Adding a windlass to a cored deck takes a little extra care. As large a backing plate as possible should be used. My backing plate is 10 inches by 3 feet of 1/4 inch aluminum. Also, you must be very careful to seal the edges where you cut through the core to prevent water intrusion. If you are not mechanically inclined this job should be left to the pro's.

Personal opinion: I just don't get small power boats. We just got back from a week in the San Juans. Small boats going fast are so loud we can hear people shouting to be heard. How can one relax with all that noise. If you are in a hurry, drive - it's faster and cheaper. Want the fresh air - get a convertible. Yesterday we topped our tank. In 9 days we used 15 gallons of diesel. A small cabin cruiser pulled in next to us and bought 160 gallons of diesel, At close to $4 per gallon that's over $600 for fuel alone!