My solution to these challenges has been to purchase and install a Harken Lazy Jack kit. There are many lazy jack systems and you will have to decide which one you think is best for your boat. You may even decide to make one yourself. After much research, including whether or not to bother with lazy jacks, I chose the largest Harken model because it would provide for three lines on each side of the boom rather than just two. Admittedly, raising the sail now requires more care not to tangle the battens in the lazy jack lines, but it is worth it! Dowsing the sail is now simple, painless, and safe. The sail comes down swiflty into the cradling arms of the lazy jack and it stays there. The result is that I use the main more frequently when I single-hand then I did before.
I did have my local canvas maker put slits in my sail cover. She finished them beautifully with inner vinyl protector and sunbrella overlaps. I am not sure how necessary this really is except that it looks very neat and tidy and covers the sail properly. It takes a few minutes more to get it on than it used to but I have a minute or two extra to spare as I linger after sailing!