Boats are designed to have their weight evenly supported by water. They will sit safely in a properly adjusted cradle or on skilfully arranged shores in a boatyard, but it's important to remember that ashore they are literally out of their element, and so need special care.
Anchor
To avoid potential damage to the hull, or any distortion where it rests on cradle pads or chocks, it is important to remove as much unnecessary weight as possible. Heavy items like the dinghy and outboard should be removed. The anchor and chain should not be left at the bow, as this area is likely to be unsupported. The same is true of liferafts on brackets at the stern. These should be removed for safekeeping to protect from theft anyway, but it is surprising how many are not!
Quite apart from these obviously heavy items, it is amazing how much weight the average cruising boat carries, from miscellaneous mooring warps, to quantities of tinned food.
It's a good idea to empty all the lockers completely. Not only is it kinder to the boat, it also enables you to have a thorough clean out. And it will save a lot of time and effort.
For if you do leave chain in the anchor locker, by the spring there will almost certainly be rust streaks down the hull below the drain holes. Equally, food tins left in lockers are likely to leave rust rings.. It's a lot less trouble to do the clearing up now.
Liferaft
Take everything that was on board the boat home and sort through it, with a critical eye. Send the liferaft for service. Blow up the lifejackets and check that they are still airtight. Check whether their gas cartridges need replacing.
Make sure foul weather gear is properly rinsed and dried before being put away. All this expensive kit will last much longer with a bit of TLC.
It's a good idea to leave fire extinguishers on the boat, especially if you are leaving the boat connected to shore power, but now is the time to check whether they are due for replacement, and to order new ones if necessary.
Flares
The same is true of flares. Contact the Coastguard about disposal of out of date flares. They will take them free of charge. Suppliers now require a fee for this service.
And if you have room at home to store the bunk cushions, curtains etc it's a good idea to do so. They will get damp and probably mouldy if left on the boat (unless there is a dehumidifier running.) Taking them home to dry out properly will prolong their life.
All the effort put into clearing the boat (and it's amazing how many car loads of stuff come out of even the most pocket-sized cruiser) will be repaid in the spring, when the gear is all ready for the new season.
You will be helping the boat itself survive the winter better, too. Don't be misled into thinking that gear left on board will help keep her weighted down and more secure in the cradle. Most of the weight of the boat is in the keel. So the less weight there is in the hull, the lower the boat's centre of gravity will be, and the safer and more secure she will be, ashore and out of her element.