After hoisting I always tie the halyard off on a nearby cleat even though it's on the self trailer.

I think ditching the reel winch will be a good change. We had one of those for the first 15 years or so on my dad's boat. No easy way to brake the douse.

Glad you like the shape of the new sail.

We are about to start our last daysail of the season, crossing the Thames estuary from Ramsgate to Ipswich where we'll winter. The currents here in England have been interesting, you really have to pay attention and plan around them. My respect for UK/French sailors who have to deal with this on a regular basis has increased substantially

Max