Migrating Itunes to a new music studio iMac

From: MacPro1.1 3Ghz Quad Boot drive is SSD. iTunes content is on a secondary 2TB drive

To: iMac 27' Retina 4Ghz Boot drive 512SSD 2 Ext Thunderbolt enclosures. I want to store the iTunes folder on an OWC Thunderbay Raid1 volume.

I had a some files that caused conflicts in the regular migration process after ten years of no clean installs. I went trough about six hours of phone support and the Genius bar before being told my files were at fault. I'm having to bring everything I need over piece by piece and install as I go. I've installed ALL of my music software, plugins and samples from scratch.

I need to keep all of my playlist info intact The computer is part of a home recording studio. The date added info and info I've added over the years is very important so I'm hoping to transfer it as is if possible. I made a backup at one point in time by dragging the entire media folder over to a new drive only to find when a hard drive went bad that the date info for all 12,000 songs was updated to the current date when I completed the drag. Id like to avoid that now if possible.

I have not signed into iTunes on the new computer. I'm not sure even how to make certain that iTunes will recognize that I'm the same user. Both computers are connected to an Airport Extreme by ethernet cables. Do I need to connect them directly to do the migration process?

Some users have suggested online that moving the entire user folder over to the external drive to free up space on the boot drive is a good idea. Would that be wise in my case? I have 120GB of iTunes content and a bunch of music plugins that insist on residing on the boot drive. All sample content lives on a Toshiba 4TB Raid.

Will the same process be followed to transfer iPhoto content?

Sorry for the multiple inquiries and if these questions are answered elsewhere. I did search prior to asking. Thanks for your time.