Generally 60 lbs. of honey would get your hives through the winter, depending on how far south you are, you may be able to get away with less. I for one, would rather leave them with more than enough to get through the winter, if they have left over stores come spring, I can harvest it then.
As to the amount of bees you will need, there is no set number. Some have made it through Michigan winters with 5 frame Nucs. Again, greater numbers will increase your chances of them making it through.
If you have a boomer of a hive, you can split it late in the summer, and hope you have a good enough flow and a successful mating of the queenless half. If it looks weak after the brood rearing has shut down, re-combine.