Thanks for the quick responses!
Yeah, every couple of years I open the iMac up and vacuum it out. And I'd upgraded the PATA disk to 500 GB some time back. So it's maxed out.
As far as VectorWorks, I appear to be out of luck. All of the installers and updaters I can find require Mac OS 9, which is no doubt what I was running back in 2002 or whenever. 10.5 doesn't know what to do with a .bin file, which is on the updater disks and also on the 9.5.3 page that rDesign cited above.
I assume that the installers also installed a Mac OS X compatible version, which is what runs now. But there's no Mac OS X installer to be found.
Any experience with the monthly subscription model for VectorWorks 2020? I don't use it often, so is it a problem to let it lapse and then restart periodically?
Finally, for my current project I don't need anything nearly as sophisticated as VectorWorks. Can anyone recommend a less expensive program that will let me draw walls with doors and windows, add a roof, and print out plan views and elevations?