Sharing existing song list between Gen 2 Nano and new Shuffle

Question

I use a desktop runing Win XP for my iTunes Library and have 1 Playlist for all songs - currently 467 song titles using 1.78 GB of memory
I have a Gen 2 Nano - all software is up tp date
I have a new car with a direct conection for an MP3 player to the sound system.
I intend to purchase a new Shuffle for the car but it will have no where near enough memory to hold the entire play list therefore I want to load the shuffle with music by "selecting" specific song titles, one at a time, from my overall playlist.
Questions:
1. Will I have any problem loading the Shuffle from my existing iTunes library? If the answer is that this is possibler to do then -
2. Specifically how would I proceed to select specific song titles from my iTunes library for copying to the shuffle? I am computer challenged and would need step by step instructions.
3. How will I designate certain songs for the Shuffle without dragging and droping them out of the overall iTunes library to a second library for the Shuffle i.e _I much prefer to keep my total iTunes Library intact and not designate certain song titles for the Nano and others for the Shuffle_.

Answer 1

When I connect my Nano to my computer it apparently compares the current total music list with the list in the Nano. If I have added a song(s) anywhere in the playlist it adds them to the Nano - automatically. If I have deleted a song(s) from anywhere in the play list it deletes thhem from the list in the Nano - automatically. If I have downloaded revised software from iTunes it downloads the changes - automatically. All of this is occurs automatically as soon as the Nano syncs with the computer. Questions -
1. When I attach the Shuffle what will prevent it from trying to automatically load the entire Nano list into the shuffle as soon as it syncs?
2. Will all of this become clear once I have registered the new Shuffle to the same name and computer that the Nano is registered to?
As it stands I expecct Santa Claus (in the form of my daughter) to present me a new Shuffle on Christmas Day so I am just trying to anticipate what I'll need to know what to do to load the Shuffle from selected songs in my computer which has never been connected to anything but the Nano.
I very much appreciate your help so I thenk you in advance.