Missing e-mails !!

If you are using Outlook forms on certain folders in Outlook, you need to set the form so that, when sent, it is saved to a specific folder. In this case, the folder would be Sent Items. The only other thing I can think is that you've got some kind of view set on Outlook that you're not aware of. You can completely wipe out any special views by closing Outlook, and hit Start-Run and type:

outlook.exe /cleanviews

If Outlook doesn't open itself, open it. Look for your emails again. Also, make sure you're Sent Items sort is what you expect it to be and that the items you just sent aren't at the bottom of the list or something like that. Click on the Date Sent bar once or twice to ensure they're going from most recent to oldest.

Really don't think it is an issue of Outlook 2K and Win98 as I have numerous users with that same setup working okay.
I would try and determine if there some sort of pattern (i.e. does it only happen when sent to a certain user or group of users? only when large attachments or attachments of a certain type are sent? etc.) Also when you say that email sent from Outlook 2K on Win2k got to the other end, is it the exact same email or only a test message?
In answer to your second question, the Exchange Administrator program does provide a Message Tracking function. However there are several settings in Site and Server Configuration that affect your ability to use this function. If the function is working properly, you can choose to track messages to and/or from certain users going back a defined number of days.
Since the problem is not occuring all the time with the same user, I would be inclined to think that the problem may be on the other end. Also, if you are the Exchange Administrator, you should be seing bounce messages, if mail is not getting through (bounce messages may be going to the Administrator mailbox instead of straight to you).

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