I'm looking for a freeware or inexpensive shareware program to
synchronize file between a Windows XP laptop and a Windows 2000
server.  Sounds simple enough.

However, I need something that does a true synchronization -- Too many
programs do a one way or two way copy/merge but don't handle deletes
properly.  I need something that handles files being added, updated or
deleted on either side, or any combination thereof, and I need
something to keep everything in synch.

It's also important to note one of the computers is a laptop, so if
the program supports real-time synchs or scheduled synchs it must
handle being offline without spewing too many errors or losing any
data.

The machines are connected via a LAN, or occasionally a VPN, Windows
file sharing is sufficient.

I have not tried this myself, but you might want to check out Windows'
built in support for doing synchronization.  It has something called
'briefcases' which act like normal folders, but they support
synchronization.  To create a briefcase, go to the folder you want to
create it in, then select File->New->Briefcase from the menu.

Also, if you don't mind a little scripting this wouldn't be hard to do
yourself.  You could use rsync along with some simple scripts to do
this.  For handling deletes you would need to keep track of when the
last synchronization took place, and what was synchronized/deleted. 
This way, if a file that was added in a previous sychronization, but
no longer exists the script will know to delete it.  When
synchronizing with other computers it's important to decide whether a
file was created again or if it simply has an old version that should
be deleted.  If the date of addition for the file is after the date of
deletion, it will re-add the file because it knows it was re-created. 
Otherwise it will delete the file.  Of course, this creates a conflict
if the file was deleted on one computer and modified on another
(similar to the problem of two sperately modified versions), but
that's unavoidable.

I played with the Briefcase a bit, but since I have several folders
scatted around my harddrive, it's less then efficient.  Also,
Briefcases tend to create orphans very quickly if you add files to the
Briefcase itself, rather then a subfolder.

I was looking at using rsync, but the delete handling has been the
biggest problem, building a system to track deletes is a big beyond my
abilities right now.

I'm starting to think I should just shell out the cash and buy
something, probably SureSync workstation initially, then possibly
upgrade to SureSync server version later on.

Thanks for the feedback though!

Couldn't you just syncronize a folder? It doesn't have to be a
briefcase. Set up in your network settings that whenever you connect
to the network, to synchronize the certain folder(s).

Offline file support in Windows?

I've played with it in the past, but the problem I ran into with
offline support is twofold.  One, it refuses to support database
files.  There might be a workaround, I haven't looked yet, the second
problem was more overwhelming.

Basically, once it decides offline mode is the way to go, I have a lot
of trouble forcing it back online until it decides it's good and
ready.  I often connect to the 'net on a slow line (dialup or 19.2K
wireless) when I need to grab a file, and in that configuration it's
impossible to get Windows to go into online mode in less then 10
minutes, plus whatever time it needs to synchronize changed files.

I'm pretty sure nothing in Windows will do what I need, and I've
basically exhaused freeware solutions at this point, so I think I'll
just go for commercialware.