What's your preferred printing solution for Mac and iOS devices?

Windows 2000 Servers??? Those are way beyond end of lifeand may be the reason you're having issues. Is this also your Primary Domain Controller?

That being said...

Windows servers don't provide drivers to Mac clients the way that they do to Windows systems. Either you provide the drivers ahead of time, or the Mac will try to contact Apple's servers to obtain them (if it is a known printer).

Second, the NetBIOS name of the shared printer matters a great deal. 15 characters or less, no spaces or punctuation.

Third, the computers that aren't bound to AD will not find them auto-populated in the "Add Printer" list. Even if you tried to add it anyway, they may not be able to authenticate properly against your print server because of its age.

Why hasn't your school sprung for a new license so you can at least get Server 2008?

What about the computers or devices that are not bound to AD. How do you connect them now?

To be able to use AirPrint, you're gonna need a much newer version of Windows and something called AirPrintActivation (http://www.airprintactivation.com). This may or may not be simpatico with any 3rd party tools you have in place for managing the print queue, charging per page, etc. (If you had a Mac server, you could use PaperCut for that. http://www.papercut.com/ )

Ahhh my mistake. I meant to say 2012, not 2000. Stupid typos!

Haha! Well in that case, are all your printer names sufficiently short? Do you find that your iOS devices only have trouble?

Also, I edited my post. Please re-read the last half.

Some of our names are 15 or less, no punctuation, but some are way more than 15, no punctuation, and some are 20+ with punctuation. I can have people begin testing to see if name is playing into our errors.

Our typical deployment involves the basic Casper way -- install it on a Mac using the Windows queue, select the correct driver, capture it with Casper Admin, and deploy it. We push out the newest Apple printer drivers to all machines ahead of time.

The issue with this (macs) is that we have pretty severe issues with print jobs just disappearing entirely once sent by the Mac, or going through but printing garbage even with proper drivers on both sides, or locking up on the Mac and never accepting authentication. We don't see these issues (as far as I'm told) when using our legacy 32-bit servers, which will soon be shut off. But as soon as 64-bit 2012 is involved, things go nuts.

We do use papercut. I've looked into getting it running on a Mac server (even though Apple doesn't provide a "print server" feature in Server.app anymore, but I'm stuck at the Papercut part. I don't believe they're currently compatible with the new versions of OS X. All the stuff they say "should" happen when you install, never happens. Note though, we are running the "slave" installer pkg, which would link back to our PC based primary. But we never make it there.. it seems to never install the web based components, so we can't access a console to configure it in any way.

For iOS, we haven't really even begun yet. We use a Clearpass server (Aruba) to enable Airplay across campus and subnets, and I imagine that will be the solution for AirPrint, but I don't want to dive into something just to find out our Windows based queues aren't gonna work.

Our non-bound machines are student machines, deployed as part of a 2:1 initiative. For now, they simply aren't set up to print at all. We've been testing with IP printing, or deploying with a "smb://servername.company.edu/queuename" but our testers have reported a ton of unreliability with that too. It seems to still be tied into 32-bit vs 64-bit windows.

The "Friendly Name" or "Description" of the printer can be
more than 15 characters, but the actual name which is used for the sharepoint needs to be short, no-punc.

Have you tried updating print drivers on the server? Are you using manufacturer specifics or generic Universal drivers? PCL or PostScript?

I haven't set up iOS printing, but for Macs, I just set up a MAC OSX Server to function as a Print Server - load the printers on there and share. On the server sits the true print management component, PaperCut http://www.papercut.com/
It integrates directly with your print server and easily syncs with AD, OD, and can also keep track of local accounts. It will keep track of all things printing to know exactly what's going on.

Printers are just manually added by students and staff under the Default listing.

We use pull printing systems for a lot of our clients sites now. It massively cuts down on wasted prints, makes it a lot more secure and means you only push out one print queue to the devices.

I fought with this in the past and never really did get it resolved well with a Windows print server. I ended up setting up my primary print server on Ubuntu Server 12.04 LTS with CUPS. The web interface for it is easy enough to navigate. You can see it on a Mac by going to localhost:631. The only con is - trying to get Windows drivers setup in an SMB share for easy printer installation is a PIT*. I ended up setting up a secondary Windows print server with it pointing to the CUPS queues. Since I set this up, I've had fewer print issues than ever.