New Mac user with several questions

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A few years back I had a Macbook but as I was working on Wintel systems everyday at work I found it a little unnatural flicking between the two operating systems everyday so it wasn't used as much as i would have like.

Anyway I now no longer do any hands on Windows stuff at work so attempting to migrate to OSX again and picked myself up an iMac.

So questions so far:-

iTunes - I have all my media on a WHS shared folder, I've imported my library to the Mac (after having to search/replace file locations in the library.xml file), everything shows up in iTunes (with ratings etc) but the files show as not located until I first go to my Music folder (I guess mounting it). How do I need to setup the Mac/iTunes so it knows where these files are automatically?

News client - On the PC i've used Newsleecher for years and found it a great piece of software, what is a recommended alternative for OSX (with the ability to search groups)?

Mail/Calendar/Contacts - On the PC I was an Outlook user but to be honest I've been going off that for some time. I'm looking for a client that can access three email accounts (2 hotmail and my personal domain) and sync happily with my iPad and iPhone.

I'm sure I'll have a load more questions that I'll add to this thread as I go but would also appreciate any tips/recommendations for others that went PC to Mac.

Thanks
Andy
 
I've got most things working now but still looking for a good newsreader, both unison and sabnzbd appear to be popular. Are there any that offer a searching service like Newsleecher?
 
Been using Unison for a few days now, does what I need to happy with that.

Next question :D, What file/sync utility for replicating certain folders to a remote network location? (Previously I used either SyncToy or just a simple RoboCopy script with my Windows machines)
 
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