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Kris is right on. Running Windows 98 has risks from data loss when your computer fails! If your existing vendor is still in business, see if they have a migration path for your data. If they are not, look for a vendor that will work with you to import your data into a new system.
If it was a payroll system, you wouldn't wait until it failed, so don't risk it with your maintenance system.
Kris and HarryK make some good points. One problem frequently encountered by not upgrading the CMMS system regularly is when a corporation decides to upgrade its servers and operating system. Often the corporation finds that older version of a CMMS will not run on the new servers or operating systems.
Most CMMS vendors provide a migration path for upgrading the CMMS, but some organizations are reluctant to upgrade and want to stay on their old system. Staying on the older system often proves more costly in the long run.