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I'm going to skip asking why he is using Win 95 as, if he is using it for some sort of billing or POS purpose, he may have no control. As for the Word Perfect issue, this was a known issue. There was an issue with a specific print driver hanging up to Win95 on boot. Win95 would see the driver on start up but not know how to make the association (which is why you had to start Word Perfect.)

To fix this, you can remove and upgrade the printer driver. To do this:
Click on Start
Click on Settings and than Printers
Use your Windows CD to reinstall printer drivers
NOTE: If you happen to have network printers, start with any drivers that may be offline or you can no longer connect to. Fax drivers, Adobe® Distiller, PaperPort® are also considered printer drivers by WordPerfect and could also be causing problems. If you happen to have PaperPort v7.0, please visit PaperPort’s website at http://www.scansoft.com and obtain the latest Service Pack for your product which addresses known compatibility issues with WordPerfect.

Another way you may be able to fix this, without upgrading Word Perfect drivers or your OS, is simply to move Word Perfect into your startup folder so it starts w/ your machine.

You can also attempt to restore the stored print information for Word perfect. This is a last resort, but to do this:
Click on ‘Start’ and go up to ‘Run’
Type in regedit into the ‘Open:’ box. Click on ‘OK’
Scroll up to the top of your screen until you see ‘My Computer’
Browse to HKEY_CURRENT_USER\SOFTWARE\Corel
Right click on the folder ‘PrintEngine’ and go down and left click on ‘Rename’. Change the name to PrintEngineOld
Browse to HKEY_CURRENT_USER\SOFTWARE\Corel\WordPerfect\13(or '12', '11' or ‘10' if your using that version)
Right click on the folder ‘Envelope’ and go down and left click on ‘Rename’. Change the name to EnvelopeOld
Scroll up to the top of your screen untill you see 'My Computer'.
Click on the ‘-‘ to close the folder ‘HKEY_CURRENT_USER’
Click View, Refresh.
Close the registry editor.