Basic file moving question

i must be numb. embarassed to say that i need a little help in understanding the easiest way to move songs into (1) a static play list, and (2) over to the ipod.
Here is the set up - I have about 10K songs in itunes and I need to go through the entire list and pick about 1000 songs to put into a static play list. I am using a wireless keyboard/mouse combo, (like a trackball) so my drag/drop capabilites using the cntrl button are pretty clumsy. very difficult to use highlighting 1000 songs. I was hoping that I could use the check boxes as a way to identify songs that I wanted to put into the statis playlist (folder) and then somehow click a button (or a similar) to say that I want to move all the checked files into my playlist. is that possible? any other options?
*one footnote here, i understand how to set up smart playlists, but the group of songs I want to aggregate has no common thread (or primary key). So i have to set up a static play list and manually choose the songs.
somehwat similar, i have a question on how to move a select group of songs (lets say 4000) over to the ipod (vs just a playlist in itunes as discussed above). i am hoping that i might be able to leverage the check box as well.
thank you for your help in advance.

Select the iPod in iTunes.
Select *Sync Music*.
Pick Selected playlist in the drop down and pick the playlist(s) you want to put onto the iPod.
Add or delete from the selected playlist(s) to put on or remove from the iPod.

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Hi sblemings,
Welcome to the community.
I think with your scenario you should ask yourself, how complicated do you want the setup to be and how much time would you have to be able to resolve an issue should one occur with this setup.
All the options that have been advised would work but they come with complexity and therefore time.
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Sorry to ramble but any advice really would be greatly received!
option 1
Would be a way to achieve what you want, it would centralise your files and you would only need to backup your file server (as long as all the files you wanted backed up were on it). This could be achieved either using the client and sharing various folders or using Server which would give you more options than you would possibly need.
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This is exactly like option 1 except that you wouldn't have to administer another mac however you may limit any future growth.
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This option I probably wouldn't pick, you could achieve this with firewire and use a firewire to thunderbolt adapter (saves you having to buy a new iMac)
option 4
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Hope this helps, and by all means any questions please ask.
Dan
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