All in all, do you use this server for E-mail only? Or do you authenticate Windows users thru it?
A file server etc etc. What's all the functionality you want with it. do you have any plans to expand or add functionality to it in the future?
Samba is what comes up naturally when you talk about linux and windows mixing together in a enviroment.
The recent release of Samba 3.0 added greatly to the fuctionality of using a Linux machine as a domain controller. However like all things new it has yet to be seriously proven in the real world. The creaters of Samba, of course, went thru serious pains to make sure that 3.0 will function correctly and as documented. It has been a long time coming and seriously large amounts of testing and proving went into it before they released 3.0 as stable. Otherwise if your still not sure the Samba 2.x series has widespead adoption and testing and documentation. 3.0 should work, and if it does, it does (if you get my drift).
heres a fairly detailed document describing how windows domain function and how Samba fits into it and it's capabilities.
Irregardless I would recommend that you keep your w2k box for the time being and get a cheap computer (maybe a unused desktop) and test out using Redhat or some such OS on it for a while till you get comfortable and are able to get it to do everything that you need it to do, before retiring the old w2k installation.
If a actuall exchange replacement is what your looking into, you can check out
opengroupware.org. Combining this with OpenOffice.org may provide a means to ween yourself off of windows products, or at least save yourself considurable amount of money.
But I think that Opengroupware is something that is still kinda new, and I have no experiance with it. Although it may be worth checking out. It's seems also that you would have to set up a email server in addition to it.
Another thing to look into is using Sendmail or Qmail to act as a email server. <a target=new class=ftalternatingbarlinklarge href="http://
http://www.tldp.org/HOWTO/Qmail-VMailMgr-Courier-imap-HOWTO/">something like this maybe?</a>
unfortunately my personal experiane is limited in situations like this.
If your worried about your non-guru-ness, you could always buy support from Redhat. That way you have their experiance at your disposal if you were to run into problems. For instance the standard edition of Redhat ES (their midrange server product) costs 799$ and for technical support you get:
Standard Edition provides a full year of Standard support (includes Monday-Friday 9 a.m.-9 p.m. phone support with four hour response (9 a.m.-5 p.m. outside North America) and a one-year subscription to Red Hat Network. Customers ordering Standard Edition will receive a full boxed product with CDs and printed documentation.
This is designed for servers up to 2 cpu's and up to 8 gigs of Ram operating on x86 style hardware.
:: Capabilities
* Mail
* File (SMB/NFS)
* Print
* Accelerated Web (tux)
* Advanced Firewall (arptables)
* Extended Remote Shell Access/Mgmt
* DHCP
* DNS Nameserver
* Network Authentication (Kerberos)
* News
* Backup
* Dump Server (Netdump)
* Directory Server (LDAP)
* SSL
* Remote Boot/Image Server
This would give you a good leg up on your Linux conversions and hopefully make it relatively trouble-free.
The basic edition is $399 and doesn't include the cds/documentation mailed to you, and loses the phone support. However you still have support via the subscription to "redhat network".
(just a idea)