1) I was thinking to boot from a Live DVD (i.e. Ubuntu). Anything wrong with that?
Nope, any FreeBSD or Linux install or live CD (like FreeSBIE or Ubuntu Live disk) should work as long as it includes the dd utility, which is very small and
should be present on any useful live CD.
2) Do I need to copy each partition manually? Or will I be copying the whole disk 1:1?
No, you can just copy the whole disk by specifying the whole disk device for your source and destination drives. It is
possible to copy just single partitions at a time if you wanted to but unless you put them in the same places on the destination disk you would have to manually make a new partition table for the destination.
It can be handy, though, if you're trying to back up a single partition to a file on a destination filesystem for safekeeping or to mount them from a virtual disk linked to the file, etc. instead of a whole disk, like:
dd if=/dev/ada0s1 of=boot_partition.raw bs=128k
dd if=/dev/ada0s2 of=system_partition.raw bs=128k
(...this example uses FreeBSD's device naming...)
etc... would make separate files in the current directory for these source partitions.
3) What if the destination disk is slightly bigger (i.e. 76.3GB and source 74.9GB)?
No problems, you will just have a some free space at the end of the disk that
could be used to extend the last partition or create an additional partition or whatever.
4) What if the destination disk is smaller?
If the source disk has a partition extending into that region you're going to need to shrink the partition first before you copy or else you will be missing the end of the partition. You can easily use a program like gparted to do that for most parition types as long as it isn't full so can be shrunk. Even Disk Administrator will work for most Windows partitions, obviously.
My intention at the end is to have a whole backup of the original 80GB 2.5" PATA HDD on a 40GB 2.5" PATA HDD. This requires to resize the Windows 2000 partition only (not all partitions).
For that I want to do a 1:1 backup to a 80GB 3.5" HDD. From this HDD I want resize the Windows 2000 partition and THEN do a second clone to the smaller disk (partition wise).
Is this possible?
Most certainly, and that is precisely what I would do. Make an exact copy first so you can't accidentally lose anything, then shrink the partition so it will fit on the smaller disk and copy that.
I do this all the time to move people's current HDD data onto a SSD... Often a significantly smaller SSD than the source HDD.
Easy, peasy....
Just make sure you get the disk numbers correct before actually executing the dd command! FreeBSD's "camcontrol devlist -v" command makes this very easy. On linux, you need to cat a bunch of stat files in /dev/ to check each device or rely on your kernel messages when you boot or plug the disk(s) in on an already running system.