Upgrading Server

Hello all!  This is my first post, and everyone here seems to nice!

Okay, here is what i want to do. I'll start off with what i got.

Our main office: We here have a server that is a Proliant ML370, running Windows SBS 2000 with SQL Server, which is the key to running our business software. We do not use Exchange, or anything really besides that to host  our software, and data storage (pictures, word doc's and so on)
When i started working here a few years ago we had 7 people running on the server, now we have 30 and are planning to move our office.  
It is a domain server, we connect our java based software through it by mapping it to a shared drive over the server and connecting a ODBC file system.
plays the rolls of:  Print Server, Browse Master, Domain Controller, SQL Server, Terminal Server, Time Source

On the road : We have 2x IBM T30 laptops running SBS 2000 (1 being a backup) running now 40 laptops also used as a print server. Basically doing the same thing we have running at our office except internet access. We travel around the United States and deploy our server at each site. I connect it to switches and we go off that.  I set it up maybe 10-15 times a year.  I already had to change the screen, fans, and keyboard. I’m scared something like the 40gb 5200rpm drive is next.

I’m basically scared to touch anything because it’s so old..  Now since we keep adding employees I’m scared the server(s) are becoming old and inefficient. We hope to have everything updated by June.

My question is:
For our office:
1. How can we migrate from SBS 2000 to SBS 2008 or SBS 2011? Or whichever one you guys would recommend. Iv been reading up on VMware and Hyper-V would that be a good route to go?
2. Right now we have a 24 port Cisco Switch, I have taken a few netgear switches to make the other desktops work. Is that okay to do?
3. We have 30 CAL’s on our home server, would we be able to keep those? Or do we have to purchase all new CAL’s? I’m not 100% how the CAL system works.
4. What software would be best to deploy and install software on the client so I won’t have to do it manually?

For the road:
1. The laptop bogs down when we do any queries or print.  I would like to see a mini tower running a RAID and so on, what are my mobile options for this? . What hardware would you recommend to run an operation of 40 and growing laptops that go on the road every other month? Mind you we need two servers one being a complete duplicate of the other.

2. Would we have to purchase another server OS to add to the road server or could we use the new OS we purchased for our home server?

If anyone has any questions please ask, i know i might be forgetting crucial information

Who is Participating?
Cris HannaConnect With a Mentor Commented:
What's important to remember in all of this is that each of your separate SBS 2000 servers, though they may have been named the same, unless the Office one was created, then imaged and restored to each laptop, and refreshed as such on a regular basis, are actually separate and unique domains.

Workstations which belong to one, would have to be disjoined from one, and then joined to the other, unless done as I indicated.

And unless you are licensed under Software Assurance, which allows for 1 "cold standby", the only way you'd be in legal conformance is 3 separate OS licenses and 3 sets of CALs

Now with all that being said, before making the move to either 2008 or 2011 is to verify that your Line of Business Software (LOB) will run on a 64 bit Operating System.  Both SBS 2008 and SBS 2011 are 64 bit OS

As for your traveling hardware...consider the HP Microserver...If you disable the Exchange and Sharepoint Services..the 8GB of ram should be enough

Microsoft has not created any white papers for going from SBS 2000 to 2008 or 2011.  My suggestion is that you contact sbsmigration.com.   Jeff is the considered expert in all scenarios for migrating from SBS, to SBS or between versions of SBS and you get exceptional support for 90 days.

I don't work for sbsmigration.com, nor do I receive compensation for recommending it,  but Jeff Middleton, the owner and I are both SBS MVPs and I've know Jeff for years.   His migration methods have been used by thousands with excellent results.
Jim P.Commented:
As a non-admin comments:

You are still in the SBS range -- but you need to decide which way your business is going. Would you be better off paying for and moving to standard edition?

Unfortunately, I can't give you advice on this. I have always been in situations where we had full domains with offsite BDC's so we were always "up".
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