Folders or Playlists-How To Make

They are called playlists. You create them in iTunes, and sync them to the iPod.

This description is for the current version of iTunes (version 12). To create a playlist in iTunes, first show your music library in iTunes (click the Music button at left end of horizontal bar). Near the middle of horizontal bar, click Playlists. A sidebar appears along left side of window, showing your playlists. At the bottom of sidebar, click the Plus sign and select New Playlist. Name the playlist as desired.

In the sidebar, under Library, click Music, to show your music library. Scroll the sidebar (in necessary) to show your new playlist (without selecting playlist). Drag/drop the songs you want on the playlist, from your music library to the playlist. Alternately (instead of drag/drop), you can right-click a song (or selection of songs) in your music library list, and Add to Playlist -> [name of playlist]. Create as many playlists as desired. You can put the same songs on multiple playlists; iTunes only loads each song once on the iPod, even if it's on more than one playlists.

After creating these playlists for your iPod, connect the iPod. Select it in iTunes (click it's device button on horizontal bar) to show its settings screen in iTunes window. Along the left side, under Settings, click Music. The iPod's Music settings screen is shown to the right.

NOTE: Any songs on the iPod that are not in your iTunes library (on the computer) will be lost.

Checkmark the box for Sync Music, if it's not already. This turns ON automatic syncing. If your iTunes music library can fit on your iPod, you can choose the option to sync Entire music library. Click Apply to sync your music library to the iPod, including all playlists. If your iPod was already set this way on the iPod's Music settings screen, you just click Sync to add the new playlists to the iPod.

If the iPod does not have enough storage capacity to sync your Entire music library, on the iPod's Music settings screen, choose the option to sync Selected playlists, artists, albums, and genres. Below that, under Playlists, find and select (checkmark) the playlists you created for the iPod. Click Apply to sync those playlists to the iPod. This option may be appropriate for your iPod nano, which has lower storage capacity.

Going forward, you can update those playlists in your iTunes library (add/remove songs). The iPod does not need to be connected. The next time you connect the iPod (or click Sync if already connected), iTunes updates the iPod with the same changes.

If there are songs on the iPod that are not in your current iTunes library, you'll need to off-load songs from the iPod. But first, did you previously import those songs from your music CDs on this computer? If you did, it's possible those song files are still stored on this computer, but your current iTunes library does not know where they are located. If you can find such song files, that are stored on the computer's drive but not in your iTunes library, you can add them. Use the File -> Add to Library command in iTunes, OR you can just drag the song files (or the folder that contains them) from a Explorer window to the iTunes window (and drop on your music library).

If the song files are not on your current computer (and there's no backup), you can off-load them from the iPod. However, iTunes syncing is generally in one direction only, from iTunes library to iPod. You cannot use iTunes to transfer song files from iPod to computer (except for songs purchased from iTunes Store). But there are third-party methods and utilities that can transfer from iPod to computer. If you do an Internet search on something like "ipod transfer music," you should get some links (including an article by CNET on the topic).

NOTE: The other option is to import the music CDs again, using iTunes.

Once the song files are on your computer's drive, add them to your iTunes library. After confirming all of your songs are in your iTunes library, you can follow the steps to set up automatic syncing between iPod and iTunes library. It may still erase your iPod when you set it up, but that won't be a problem because your iTunes library has all of your songs; they get synced back to iPod (based on how you set up the iPod's Music settings screen).

The last two songs I just purchased yesterday on iTunes did not load to my iPod.

If you purchased them from the iTunes Store, they should sync to your iPod. But they have to be stored locally on your computer's drive. Purchased songs can be accessed (and played) in iTunes by streaming from Apple's iTunes Store servers (also called "iCloud"), even if they are not downloaded. You can check by showing your iTunes music library using the Songs view. Click on the control at the right end of the horizontal bar (in iTunes window) so that it says Songs, and your iTunes music library is shown as a plain list with columns.

If the iCloud Download column is hidden, make it visible (right-click the heading row of song list to show/hide columns). The iCloud Download column is narrow with cloud symbol in its heading. If you see a cloud with down-arrow symbol in the iCloud Download column for any songs on your library song list, those songs are being accessed from iCloud. You can click the cloud with down-arrow symbol to download that song. Scroll through your song list and look for any songs with that cloud. If you see a lot of them, you can sort the song list by the iCloud Download column (click heading for column), so that they all appear together on the list. Select them all at once, right-click selection, and Download.

Should I delete them from the iPod or just delete the whole iPod and start over?

When you set up automatic syncing, as described in first reply, iTunes syncs the iPod based on how you set up the iPod's Music settings screen. It does not matter what is currently on the iPod. For example, with the iPod nano, if you set it up to sync selected playlists, after clicking Apply, the iPod nano will only have the songs on those selected playlists (plus the playlists). If you set up the iPod classic to sync the entire music library, it will have all songs (and playlists) in your iTunes music library, after clicking Apply.

You can "delete the whole iPod." That's called doing a Restore. The Restore button is on the iPod's Summary settings screen in iTunes. This erases the iPod, reinstalls its software, and sets it to default setting.

Use iTunes on your Mac or PC to restore your iPhone, iPad, or iPod to factory settings - Apple Support

If I reformat the iPod will my purchases download to it?

If you do a Restore using iTunes, songs (including purchased songs) in your iTunes library, that are stored locally on the computer's drive, will sync to the iPod, based on how you set up the iPod's Music settings screen.

Sounds like you answered your own remaining questions. 🙂 As an FYI...

- When the iPod is set to use automatic syncing (with the Sync Music setting), you do not need to Eject it in iTunes (or in Windows) before disconnecting. iTunes automatically unmounts the iPod's storage disk when iTunes is not actively syncing to the iPod. Although the iPod is still visible in iTunes while connected, it is safe to disconnect it. Just look at the iPod screen before doing it. If it says "Connected" or "Do not disconnect" on the iPod's screen, then don't disconnect it; either iTunes is syncing the iPod (or you DO need an Eject for some reason). Otherwise, you can disconnect it.

- But if you want to have the habit of clicking Eject before disconnecting iPod, you can still do an Eject in iTunes (and the iPod disappears from iTunes). In iTunes 12, the Eject button in iTunes is next to the iPod's name (when you select it in iTunes). It looks like a triangle with a line below it.

- Also, When the iPod is set to use automatic syncing, it probably does not appear in Windows Explorer most of the time. That's normal. If you want it to appears in Windows Explorer all the time while it's connected, select the iPod in iTunes to show its Summary settings screen in iTunes window. There is a setting for Enable disk use. Checkmark that box and click Apply. When that setting is ON, iTunes keeps the iPod's disk mounted continuously, like when it is set to use the manually manage method of loading songs. Therefore, you'll need to Eject the iPod in iTunes before disconnecting it. Unless you have a reason to have Enable disk use turned ON (like you copy and store files on the iPod using Windows Explorer), you should leave it tuned OFF (to reduce the chances for data corruption on iPod).