How can I manage 2000 machines ?

Nadir, You wouldn't happen to be located in st. louis, would you??
I would just love to know how you landed a gig maintaining 2000 units- but that's besides the point-
IF you're in St. Louis or close, I can help you.  I could refer you to some articles as well, but in this case, you're going to be needing more help than reading some articles. Sounds to me like you need either a consultant to work with and advise you on the project, or you need a business partner-

If this is going to be a one man job, you might want to schedule the rest of the year to do it in...   Just kidding, of course, but I will say that you have your work cut out for you...

That being said, a friend of mine in CA did over 10,000 upgrades and 25 server upgrades in 1 day..  It took 3 months of planning to do it however..  I am waiting to get a chance to sit down with him and hash out the entire process..

I do know that he used a combination of Sysprep (for the servers) and Riprep for the clients.  So my suggestion is to think about setting up a RIS server and pushing the images out from there.  The problem you would have with Sysprep would be the time it takes to install all of the hard drives.  Now, in your situation, I can see some hurdles here, as the NICS must be PXE compliant, but you can get around this with PXE boot floppies.  here is some reading on this approach:

http://www.microsoft.com/technet/prodtechnol/windows2000serv/deploy/depopt/remoteos.mspx

I believe you can install the RC with the RIS image, so that is not an issue...  (winnt32 /cmdcons)

As mentioned above, you can install Terminal Services client on the 98 boxes, but that will not give you access to them..  XP Pro is the only OS right now that allows client remote access.  But you can install something like vnc or tightvnc.  Of course, this will have to done on each client.  Never tried to install something like this via Group Policy on a pre-W2K machine..

And digg answered your #4 question correctly, as far as I know...  nothing to offer you here..  

Really, I wish you the best with this..  I would love to be involved in this project also, as I think it would be quite a learning process.  But be ready to do a lot of testing before proceeding...  Preparedness is the best remedy for success..

FE

Well... if you're in Northern California, I might be able to help as well :-P

Anyway, to me the tricky part is not the number of workstations that you've got, but the combination of differnt type of workstations, software, data storage location, that'll get you.

If the machines are fairly the same, ghosting would be the way to go.  You'll probably spend a lot of time transferring the data from the workstation to another location, then move it back, though..  If the company is fairly organized, where everybody is storing their data in a common network drive, then you just saved about 60% of your time.

I agree with FE that I am not sure if there is really a way to install Remote Desktop on a Win 9X client... better tell your boss that he should "deferr" this part of the project 'til AFTER everybody is up to XP.  Otherwise use VNC.  Another thing is that if you just want to use the VNC client, you can actually do a RDC connection using the Internet Explorer now, that shipps with Windows Server 2003.  The asp aplet can be copied and pasted to another win2K server w/o a problem.

So.. it really depends on how everything is setup over there.  I don't think you can do everything in one day, but I can tell you that planning is 1/2 the battle.

- Info