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Operating System Reccomendation Sought

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So, I have this non-engineering question.  I am desperately calling upon my fellow engineering brethren to help me out.
 
I recently had a computer hard drive die on me and had to start over.  That being the case, I asked a couple of people whether I should stay with Widows 98 or change to Windows 2000 or XP in hopes of stabilizing the platform.  I was amazed at the lack of consensus among the response I received.
 
So here I go.  Firstly, I do not wish to create a kind of LORD vs. ASD debate.  I am simply at a crossroads, and sincerely want to improve the stability of this silly box my life seems to be so dependent upon.
 
3 computers - 1 server & 2 work stations - with potential to add two more over the next 18 months.
 
Windows 98 - Server, P3-350 w/ 256 megs of ram
Windows 98se - Work Station #1, P3-733 w/ 256 megs of ram
Windows 98se - Work Station #2, P3-650 w/ 256 megs of ram
planned new work station, P4-2000 w/ 512 megs of ram
 
Data is kept on Work Station #1 and the server is used for print sharing and backup.
 
My question.  #1)  Do I change to Windows 2000 on all machines.  #2)  Do I change to XP on all machines.  #3)  Or, do I stick with Window 98 and upgrade the server to 98se.
 
The goal is to stabilize each individual machine.  The network seems to work just fine.  It's the annoying little hang-ups, lock-ups and crashes that bug the day-lights out of me.  I don't know for sure if it is the software that creates these problems or the operating system.  I am lucky that I haven't lost any data (yet).  The machines do not handle opening and closing several applications at the same time without noticeable memory leak and we have to occasional reboot to get 'em humming again.
 
The software I'm running seems to be fairly standard for our industry.  AutoCAD LT2000, Office 2000, Visual Analysis 4, Quick Books 99, Backup Exec, Outlook, Internet Explorer, Digital Camera stuff, 3 different printers (all HP) and "plug and play" stuff (yeah, right).
 
I of course don't want to trade stability for conflicts.  Seems to me that in the era of the P4, I should be able to have both.
 
The former Microsoft employee programmer next door says 2000 all the way.
The owner of the computer store where I buy my stuff says 98se, but he likes XP the more he plays with it and don't even think of 2000.
The kid who cleans my office and is a self proclaimed guru (he actually fixed a major crash and showed me that even though my computer would not boot up because it couldn't find my hard drive that it was actually not my hard drive, so he has earned some credibility bucks with me, and he is only 16 year old, amazing!) recommends XP and staying away from 98se and says even 95 would be better than 98se.
 
Please help!!  I am pretty good at tinkering with hardware and drivers for peripherals and loading software without blowing things up.  But, I am no means an expert.  Also, since the system is so small, I would rather administer it myself than hire it out.
 
Thanks in advance for your input.