Apple has a "Legacy number" - 1 800 767 2775 - specifically for old computer running obsolete OS versions. I am unsure what the charge would be if you call them, but you can try.
What issues are you having?
If the computers are running OS 9, then they are very old, and likely you will not be able to upgrade them much. The processors in these computer are probably far too slow for the technology today.
There is a forum discussion area devoted to OS9 and earlier Mac operating systems.
Can you tell us what model Macs these are? All Mac models made since 1998 have separate forums here. If all the computers are the same model, getting you to the forum that matches yours would, I think, help you a lot.
Rather than worry about what the OS 9 computers will not do, focus on what they will do.
For example, Nashoba offered Filemaker as a WYSIWYG database option, including a field for artwork, since 1984. That was 11 years before Windows 95. Older versions of Filemaker are still going strong and allow students to learn a database without the expense of Microsoft Access. Access still is clumsy when compared to Filemaker -
Filemaker foresaw the day of digital cameras and started with a field called a "container" for clip art back in 1984. No amount of media hype and marketing from Microsoft can make up for the decade that some of us had as a head start on image database options.
The key will be to get installation software for some of the older versions of any software and permission to replicate it over several computers. Recyclers do not do a good job of getting the software disks with the older hardware that is donated.
A free substitute for Filemaker is AppleWorks or ClarisWorks. Apple formed Claris, bought Filemaker, used that access to the code to make a generic version of Filemaker, and then included that databade software with every system install disk. Teaching core concepts like data management does not require a new computer. It can be done on a fifteen year-old Mac with free software. No such luck with a Microsft product.
Post back if the Chicago user group option does not pan out.