I usually sail up to the dock and then drop the sail into the cockpit. Later, I roll it up. Normally, I don't tie up at the dock for any length, except when the dock is at the destination. In that case, I use the main halyard as a topping lift, and then I might "flake" the sail more or less on the boom. As it's temporary, I don't sweat neatness, just to get the sail out of the way.
Occasionally, I have the motor rigged and use it for the last few hundred feet to the dock. I leave the sails up, because usually the reason I use the motor is that I don't have wind.
If I beach the boat, I drop the sail pretty late, also just let it go into the boat. First secure the boat, then secure the sail. Takes a bit of planning to not drop the sail on the side where the dock is, so I can reach the dock to tie up.
This is with the old sails, which were very soft and therefore tended to "bunch" rather than flake. Also something I did in a hurry, because we needed to be somewhere before closing time. And you don't see the main acting as a topping lift (because we forgot?).

With stiffer sails, flaking or rolling get easier. Someone here described a way of flaking the sail not on the boom, but into a pocket made from the last yard of sail close to the boom, then folding that one over to help secure everything. Never tried that, but seems cool.
(I'll look to see whether I have another photo somewhere).
I occasionally go for longer solo sails (at night no less) and there are times the wind dies for extended stretches and in more confined areas (canals, between trees, under bridges). I don't always drop the sail (esp. if I think there'll be wind behind the next headland, or turn), but if I do, I would go in the same stages. Drop the sail first. If I expect I'll raise it again soon, I may leave it, otherwise I reattach the halyard as a topping lift and then secure it to the boom. Same with jib. If little wind or short time before it gets raise, I may just drop it. Otherwise I loop at least a bungee over it. Overnight I would take it off, and if I ever had to sail with it down (which would presume stronger winds) I would probably make a very tight package of it.
More ideas about reaching.
My jib cleats are not "captive", which is something I like, because I can "drop" the sheet into the cleat from above. I can pull the sheet tight from wherever I sit and then just have to be able to reach the CB (or press down on a tight line with my foot to make it go into the cleat). The other thing this allows me to do is to tie the ends of my sheet together, so that to get hold of it, I can grab any part of it. Because of open cleats, I can release and recleat without having to sit in-line with the sheet.
The other configuration that works similar is if the cleats are directly on the jib car. What doesn't work well, is CB mounted cleats that are captive. One boat (not a DS) that I sailed on had the jib cleats on the opposite deck. That works well, esp if you hike out a lot, but it will block part of the cockpit because the sheet is going across it.
I'm sure you figure it out.