I did what you said, Sethan. Restarted in DOS mode, ran scandisk C and when it finished its thing (didn't get to the surface scan part) it said the free space is being reported incorrectly, fix, don't fix. I chose fix and then this message popped up.
Not enough free conventional memory to perform surface scan.
You may need to remark (REM) some device drivers from your CONFIG.SYS fle. Or, in your CONFIG.SYS you may need to load EMM386.EXE drive to load your other device drivers into upper Memory Blocks using DEVICEHIGH= statements.
This is kind of outta my league here, but it sounds almost like a bad ram problem.