Hey Andy,
The quick answer is yes... Linux will do all you need it to and more. SAMBA will enable you to do both 1 and 2 from your questions. Squid is a great idea for a proxy server (I use it myself in our network).
Can you clarify a little more on item 3 from your list? What exactly do you mean by "Breaking the system"? Do you mean that you want to restrict their access to the main server, shares, and the documents of others? If so, Linux is IMO more capable of doing that that Windows and is easier to set up once you get the hang of it.
Also, with only 5 PCs, have you considered setting them up as Linux boxes also? I think it would be an interesting experiment to see the time needed for users to become acclimated to Linux in an everyday business use scenario.
HTH
Dave
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