Getting started again advice for a newbie

Here are the facts. I am returning to the hobbie I love. I was in retail at a small store for a/v and found it a great way to enjoy things I can not afford, but have been away since 98. I have a large cd collection of aprox 2000 cd's or more, some I care about others were used to DJ, however I would like them all stored. I have a 1 year old macbook pro. Last time I tried to load all my music on a pc I crashed it and lost everything. I am not looking to replay that. What I want to do, if it is possible, is store all my music on separate hard drive in lossless form, and to be able to back it up storing off site. My big question is, am I able transfer from the hard drive in in full size to another location such as my macbook in a compressed form. Does itunes allow this to happen yet? Bottom line can I run 2 music libraries one for quality and master storage, and one for ipodes and compressed functions nonaudiophile grade.