PC Hanging in Programs and Shutting Down

I have a workstation that is a Gateway 500C running Windows 98SE. Specs: 845 El Paso 2 motherboard and P4-478 1.6 Ghz Processor, 256MB RAM, 20GB HDD, 32MB NVIDIA Geforce 2 MX200 AGP Graphics. The problem that we are having is that in the morning when the employee arrives and boots up the PC and opens a program it will take a really long time for the program to come up. When this happens she has to reboot immediately and then the programs come up fine. If she doesn’t reboot immediately then the programs start to not respond and never recover. Also, when she does a shutdown at the end of the day she usually always gets KEEPDrv not responding, End Tax, Wait or Cancel. As long as she ends the task it will shut down properly. If she says wait it hangs. Any suggestions will be greatly appreciate.