Do places remember that you applied few years back? Is it worth another shot if I updated my experiences for relevant for the job or school?

Don't even bother.  Put them on your permanent blacklist until there are no jobs left to apply for and you're forced to leave "Unpleasantville" for greener pastures.

Take the shot !

Usually not - apply again.

Not if phone number has changed. 

depends on the place, you could try applying again