On roller furling. Never had it on the DS, but have it now on my "other" boat. Complicates rigging the boat, which is a pain if you launch from a trailer. I almost never drop the jib on the DS - but, for example, all the boat launches I use are well protected, so sailing in with all sails up is never a problem. The other boat is a bit more "spirited" so being able to "depower" conveniently is nice. Conditions are different.
On holding the sheet in your hand: K.C. Walker encouraged me to get a ratchet block - only way to go
. Makes holding the sheet so much easier. Get one of the automatic ones (e.g. Ronstan). They disengage the ratchet when not under tension, so there's no penalty at light winds (and no need to remember to switch the action on or off) - but: don't thread the sheet the wrong way - you'll look pretty silly trying to sheet in if the ratchet won't let you (don't ask how I know
)
On routine: I decided against writing things down. But I found out that taking tasks in some order is useful. As I get out of the car, I go from front to back on the boat, doing one series of tasks, from disconnecting the trailer light, to putting the Windex on the mast. On the return, I collect various bungees used to tie down things during trailering. Point is, those task are now arranged in a fixed sequence and less likely to be forgotten.
I still manage to sail w/o Windex or I have to scramble trying to get a bungee off the mast that's now 10ft in the air
. And I've tried to float my trailer or sink the boat by flooding it via an open transom drain. Stuff happens. I have separate "lists" in my head for going out with experienced crew or guests, and I leave as much connected as possible (sheets, for example). That helps.
#10: yes, I've postponed cosmetic maintenance happily once the season starts, but too often, I come off the water with a new item to fix.