Laptop stolen - now need to put ipod tunes 'back' onto new itunes......

Hi,
Well other than the utter crap of having my Macbook stolen (and changing all personal account numbers etc.), I am now trying to piece together what I can, and would really appreciate advice.
I have recently picked up a new Mac and am trying to rebuild what I lost including music:
1. I did not back up for the last few months, but have songs on my ipod Nano, that I would very much like "back" on my itunes in my new setup. I'm scared pluggin my nano into my new Mac will erase what is on my Nano - and or not let me 'sync' it. As this is the ONLY copy of certain songs I have (Downloaded from iTMS) I thought I"d play it safe and ask for advice before I go plugging and syncing....
2. My understanding is that itunes song's I've bought, if I no longer have the physical files, I can't 'redownload' them without paying again. correct?
PS. I authorized itunes on my new Mac, and drag-dropped the latest itunes library from my Backup HD.
Thanks for any and all help.

The transfer of non iTMS content is designed by default to be one way from iTunes to iPod. However there's a manual method of copying songs from your iPod to your Mac at this link: Two-way Street: Moving Music Off the iPod
If you prefer something more automated there are a number of third party utilities that you can use to retrieve music files and playlists from your iPod, this is just a selection. I use Senuti but have a look at the web pages and documentation for the others as well, they are generally quite straightforward. You can read reviews of some of them here: Wired News - Rescue Your Stranded Tunes
Senuti Mac Only
iPodRip Mac Only
PodWorks Mac Only
iPod.iTunes Mac Only
PodView Mac Only
iPodAccess Mac & Windows
YamiPod Mac & Windows
PodUtil Mac & Windows
iPodCopy Mac & Windows
The transfer of purchased content to authorised computers has been introduced with iTunes 7, look under under File>"Transfer Purchases from iPod". A paragraph on it has been added to this article: How to use your iPod to move your music to a new computer
If your iPod is set to update automatically you just need to take care when connecting to your new computer and an empty iTunes. You will get a message that your iPod is linked to a different library and asking if you want to link to this one and replace all your songs etc, press "Cancel". Pressing "Erase & Sync" will irretrievably remove all songs from your iPod. Your iPod should appear in the iTunes source list from where you can change the update setting to manual and use your iPod without the risk of accidentally erasing it. Check the "manually manage music and videos" box in Summary then press the Apply button. Don't uncheck Sync Music it will be unchecked by default when you choose the manual setting: Managing content manually on iPod
Keep your iPod in manual mode until you have reloaded your iTunes and you are happy with your playlists etc then it will be safe to return it auto-sync again.

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