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how big should be the swap partition?
Back in the day the rule of thumb was "2.5 x Amount of RAM" = amount of virtual memory you need. So if you have 500MB of RAM you need 1.25GB of free hard drive space for VM. Does this general rule of thumb still apply today where we have RAM upwards of 4GB?
There is some discussion about this already on serverfault here. On the right you'll also find several linked and related questions.
It's subjective really. IMHO I think that as long as you've got enough swap to dump all of the memory then you're fine, but it depends on the OS and how efficient it is with memory.
Ideally you won't be relying heavily on swap, but with Windows it's trivial to add more virtual memory afterwards (or a flash drive) and on Linux you can always repartition or use a swap file (eg.
dd if=/dev/zero of=/root/swap_file bs=1024 count=1048576; mkswap /root/swap_file; swapon /root/swap_file
) to up it afterwards.