Win2K AS: install Exchange 2003 or upgrade to Win2K3 SBS?

Current system:
We have a Win 2K Advanced Server, running SQL server and operating as a file server at our main office with a few machines, laptops, wireless network etc.  This is running as a workgroup only, everything on public static IP addresses with a separate hardware firewall on the internet connection.

We run hosting services in Telehouse (London) and our web server, ftp site and email server (not exchange) are located there (Win 2K AS again) - this will remain unchanged.

I've been looking at setting up Exchange 2003 on the main office server so that I can more easily synchronise my email between main machine, pocket pc, tablet pc, plus access it via Outlook Web access when I'm out of the office.  At the moment I have to do 5 syncs to get data to and from the tablet PC, via the pocket PC and its prone to error!

I now have an additional office and I'd like to enable the two employees there to participate in the network, so will setup a VPN tunnel between the firewalls (the firewalls can tunnel, but its not encrypted - I believe a VPN comes with SBS 2003).

Using Exchange will also mean that I have a single backup point for the data for all users and can host shared calendars/folders.  We also need a central document store!

I'm also looking to upgrade all users to Office 2003 (currently on Office 2000/XP) - hence the interest as I'd like to stage the upgrades, in the right order!

The question is, what is the best way to achieve this? (if its sensible at all!)

Can I easily upgrade my existing Win2K AS machine to SBS 2003 or should I stick with my existing Win2K AS + SQL machine and just install Exchange 2003 on it?

The MS site says you can upgrade from W2K Server Standard edition - does that mean only 'Server' or is 'Advanced Server' included?

Licensing costs aren't an issue as I'm in an MS partner program and have all the software I've mentioned already.

Maximum points on offer as this is a pretty complex scenario and I'd like to start the upgrades this weekend!!

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I haven't had to work with SBS 2K3 yet, but I was checking some docs on it and apparantly you can upgrade from 2K Server to SBS 2K3 but not with Advanced Server.

I personally would stick with what you have assuming you have enough horsepower. I would also upgrade that box from W2K to W2K3 first (run the HCL first to make sure your hardware is supported). I think you have to have SQL 2000 patched to SP3 in order for it to run on W2K3, so make sure that's done ahead of time as well.

Run latest critical updates and all that good stuff.
DCPromo your 2K3 box so you can get your AD going.
Install E2K3. There is a nice Deployment Guide that assists you with the installation.

As for the VPN...what kind of firewalls do you have that establish tunnels, but does not encrypt them. That defeats 1/2 the purpose.

Regardless, you can use Routing and Remote Access to make that box a VPN server and then use Microsoft's VPN client at your remote site. If you have another server out there, you could setup a sort of site-to-site VPN using IPSEC policies. But then you start getting into certificates authorities and all sorts of fun stuff. In fact, if you wanted to use the server to create L2TP tunnels instead of PPTP tunnels, you need certificates as well.

The SBS 2K3 Premium comes with Internet Security and Acceleration server which is basically Microsoft's firewall product. The nice thing about the product is that is has built in support for a lot of MS applications. You can purchase ISA server as well and install that. However, I wouldn't recommend making your core infrastructure server your firewall as well.

That's a pretty quick overview. If you have any specific questions, let me know.

krytenxpertAuthor Commented:
Well, I didnt' find any docs, but decided to just try it last night, and you're right - you cannot upgrade from AS to SBS.

Not sure if I really need to install W2K3 as I don't seem to loose much using Exchange 2003 on Win2K (the main thing is HTTP sync) and what I have works!

The Firewall is just that - they enhanced it to provide signed tunnels, but it doesn't have the horsepower for encryption of traffic on the tunnel - better than nothing!

Looking at it, I'm not sure that SBS 2003 really gives me much that we would actually use (it was really the fact that it was available and included 'everything in one go' that seemed attractive).

Really a decision of whether to upgrade to W2K3 first, or just install E2K3 then...

Any idea what version of W2K3 I need to be able to upgrade from W2KAS?

Thanks for your help.
Microsoft makes you stick with the same version, so you would have to upgrade your W2K AS server to W2K3 Enterprise.

A new feature with Exchange 2003 allows you to run Outlook 2003 over the internet through HTTPs (called RPC over HTTP). However, I'm pretty sure you need W2K3, more specifically, IIS 6.0 to run it. But as you said, if your most important goal is to have the mobile device sync feature working and that works with IIS 5.0, I probably wouldn't bother upgrading to W2K3.

There are a few feature enhancements that you can take advantage of with W2K3 (changes to Terminal Services, faster IIS, etc.) that I really like. Espcecially with E2K3 being so dependent on IIS, I prefer to see it run on an a W2K3 server, but it is definitely not required.

Let me know how it goes.

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krytenxpertAuthor Commented:
Appologies for not updating this.

I finally got round to sorting this out during the post-Christmas break.

In the end, I decided to go with a new, clean installation of SBS2003 onto a new machine as the existing W2K server is working fine and I can't upgrade W2K AS to SBS2003.  Also as pointed out, if I installed Excahnge on Win2K then the RPC over HTTP won't be available.

Thanks for the help.
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