Hi Brad,
My suggested diagnosis steps are:
1: Run Tools > ShowConfig. This will show you how much RAM is being detected in Hardware
2: From a command prompt type 'avail'. This will show you how much memory is available and in use
Together these two steps will confirm how much memory is being detected and how much is being used.
I use ClassicWB and all the add-ons consume about 4MB of RAM in total on boot. In my emulated clean 3.2 and 3.2.1 environments about 1.4MB of RAM gets used just to get to Workbench.
My last thought for now on this, have you got anything plugged into the PCMCIA Port?