Classic Troubles..

[Joe]

A friend has this trouble with Classic:

"Recently I've noticed a string of problems all linke to classic.

a) none of my classic apps launch. The little '9' icon bounces and 
stops. My applications bounce and stop.. but without the little arrow 
under them and the application doesn't do anything.

b) restarting my computer in OS 9.2.2 it never starts w/o problem. I 
restart properly but it says "It wasn't shut down properly".

So anyway I'm just trying to get my classic applications to work again? 
Any idea what I can do? "

Can you give him some advice?

TIA