When I upgrade from 095 to 096 do I need to do an item wipe and if so I need to know how to do that. I am new to all this.

nope

When I tried to upgrade it had alot of errors. I dont know if I am doing something wrong.

Updating the core is one thing, updating the scriptbase is another. If you are just replacing the core, you should have no error related to items. If you are replacing the scriptbase... expect errors related to items (and the best solution, if applicable, is items wipe).
In case you are replacing the core, probably you can have errors due to other things: you didn't recompile all your script, some of your scritps are using data in a wrong way (it was already wrong, but older core didn't recognize it as wrong), other things I can't remember...
You should post the errors