yes, just work on them seperatly
Yes, you can have to iPods of any kind on one iTunes account.
yes
Make sure the "Manually manage music and videos" check box IS CHECKED on both of your ipods. This will take a little more work but then it will not automatically sync and will easily allow you to connect multiple ipods to one itunes - we have three ipods and one itunes at our place.
There's no Ipods which does not work with the new Itunes. However future versions of Itunes may
You do not Jailbreak iTunes; you jailbreak iPods and iPhones.
1
Yes, iTunes version 9.2 works with all current iPods.
you can only use itunes on ipods
No, iTunes works exclusively for the iPods.
No cuz I got like 10 on mine
There are various solutions for using multiple iPods with one computer. Apple has a support page describing the options (See links below).
When you plug in both iPods, each should be recognized as a separate removable drive from one another on your PC. Go to computer and open both of the iPods. Then, just drag the music between the two.