Assesing a new network for a new Job

I will be working for a library. It has 4 servers and about 30 workstations.

I have listed my questions below

1. Does anyone have a list of questions that will help me asses the network

that already exists.

2. My second question is about troubleshooting software. It is the biggest

hurdle for me to face. Can any one advise me of the easiest procedure is to

do?

Thank you so much. Your help will go a long way.

Douglas