Glad you had an enjoyable, if strenuous time!
The distances you want to be paddling a DS are limited. A few hundred feet. Mostly, I have my paddles for some quick manual support while docking/undocking. For any distance, I rely on a small elecric motor. Used to have a trolling motor with two lead acid 12V batteries. Worked moderately well and is cheap. I've since upgraded to the same EP Carry system used by Tom. It does deliver a bit of additional boat speed, perhaps .5 knots. but mainly its much lighter and more convenient in use. That's worth it for me. It uses about 1/3 the electric power of the trolling motor, which should make it more practical to recharge the battery with some kind of solar panel, for example (or what I sometimes do, recharge it at the destination so it's full again for the return),
Give your trailer some attention before painting the boat. You should at least narrow down the sources of your rattle. Not all are equally problematic. The fenders on my trailer rattle and nothing I've tried seems to fix it. I have my mast suspended at three points. The center is supported near the mast partners, there's a rear support that fits into the gudegeons for the rudder (it's a simple board with pintles and a slot for the mast) and for the front I built a small wooden support that I attach to the winch post for the trailer.
The middle of the mast is tied to the cleats on the deck. Front and back are secured with bungees (to keep them from bouncing) and, in addition, a bit of rope. The latter provides security, the former limits motion of the mast within any slack allowed by the rope tie down.
I use two ratchet straps, one across the foredeck and one across the stern of the boat. The latter isn't fully adequate for extended towing as the boat can shift/rotate inside the loop formed by the ratchet (and too much tension would damage the hull). If I went trailering for longer distances I would use to separate tie downs to each rear corner.
Your stern bridle, when going upwind, should be under tension and well clear of the tiller. Mine ends in a block and therefore I have two parts of the mainsheet connecting the boom to the block on the bridle.
Here's my old setup (trolling motor and before I updated to newer ropes for mainsheet and traveler. You can see in one picture how the traveler rests on the tiller when there's no pressure in the sail (going downwind in light winds).
When gybing, I take care to shorten the mainsheet before the boom comes over and that fixes any tendency of the mainsheet to tangle with anything at the rear of the boat. Here's the updated traveler with the EP Carry.
As you can see the motor stays behind the traveler when raised and the control clears it on the outside. For longer sailing w/ the motor raised, I could loosen the screw and slide it inboard; for the trolling motor, that wasn't optional, because the motor is in the black bulb and would overbalance, so I always had to bring it in.
I'm really satisfied with my setup; I use it with a ratchet block like this:
and that gives me enough additional holding power that I don't need to cleat the main most of the time.
(PS: for a center boom setup your boom needs to be stronger than for end boom or mixed. Standard DS booms are fine, but if the profile isn't strong enough the boom could bend).
