Scott,
I think that I can answer some of your questions.
First, Bowline. Here in MN, I have only heard it pronounced Bo - Lynn', at least by sailors.
1. I am curious to hear what other Daysailer sailors say about how far much you let the sail and boom hit the shrouds. I let the sail hit the shrouds when going down wind. Your idea about putting a stopper knot in the main sheet seems logical, but sounds scary to me. I think that it is best to just cleat it off when the main gets to where you want it.
2. You want to point into the wind to raise the sails. The objective is to keep any pressure off of the sail while you raise it. This allows the sail to slide as smoothly as possible and lets you get the appropriate tension on the luff and at the foot. You can use this same technique if you see that you need some halyard or outhaul tension. Point it into the wind, tighten the line, and then fall off again.
2a. No great suggestions for you. You say that you are setting up under motor. I think that if you had some crew, leaving the motor on and having the other person keep you pointing into the wind would make it easier. That is pretty much what people do on big boats. I started sailing on bigger boats and I am still getting the hang of single handing in heavier air.
2b. You want the sheet to be loose (and the sail not loaded with air). This allows you to raise it quickly and not load it in a way that it was not intended to.
2c. I have always gone with main then jib, but maybe it doesn't matter. Since the main takes more work, I think that it is better to raise it first and not have the jib flogging on you while you do it.
3. Yes, point into the wind when dropping the sails. Reduce the tension on the luff, etc.
3a. By pointing into the wind, the boom will be running down the center of the boat and falls in a good spot when you drop the sail.
3b. I think that the order depends on where you are and what you are doing. If you are taking them both down, the order probably doesn't matter. I usually drop the jib first, but I haven't thought that much about why. Maybe the main first because when it is flogging around, things seem more chaotic? If I am going to dock, and the dock is upwind (or I can turn into the wind on the other side of the dock), I just leave both sails up. If the dock was dead downwind, I could see using only the jib because you can completely let it flog, but you may need to take the stopper knots out of the end of the sheets.
I have been sailing up to my buoy with both sails up, but the jib flogging, but I am thinking about dropping the main on the lake and then sailing up to the buoy under jib alone.
I think that you want to have the main sheet uncleated / loose when dropping the sail unless you are motoring into the wind and are sure that you won't be falling off at all. (someone on the tiller)
I think that your flying analogy is pretty good. To add to it, when you are sailing on a small lake or close to shore, you loose room/time for maneuverability. Kind of like flying close to the ground.
David.