How many songs?

It would vary as its 4gb but depending the size of your mp3 or since your ripping from CD it'd probably be a high bit rate so more space could you not clear out some space?
4gb usually holds 1,000 songs based off a 4 minute interval

To download songs to iPod nano: m Simply connect iPod nano to your computer. If iPod nano is set to update automatically, the download begins. Important: The first time you connect iPod nano to a computer, a message asks if you want to transfer songs automatically. If you accept, all songs, audiobooks, and other items are deleted from iPod nano and replaced with the songs and other items from that computer. If you don’t accept, you can still download songs to iPod nano manually without deleting any of the songs already on iPod nano. While music is being downloaded from your computer to iPod nano, the iTunes status window shows progress, and the iPod nano icon in the Source list flashes red. When the download is complete, a message in iTunes says “iPod update is complete.” If you set iTunes to download music manually, you can reset it later to update iPod nano automatically. For more information, see “Updating iPod nano Manually” on page 22. To reset iTunes to update iPod nano automatically with all songs and playlists: 1 Open iTunes and select iPod nano in the Source list. 2 Click the Options button and click Music. 3 Select “Automatically update all songs and playlists.” The download begins automatically.
if you need further assistance please let me know. Thanks, MIDWEst-tek

The ipod nanos the smallest product in the Apple iPod line. The fourth generation Nano comes in two different capacities, each capable of holding thousands of songs.

Capacities
1. The fourth generation iPod Nano comes in 8 GB and 16 GB models. The 8 GB version can hold 2,000 songs, and the 16 GB version can hold 4,000 songs.
Tips
2. Song capacity estimates are based on music encoded in Apple's proprietary format at a standard, average bitrate. The higher the bitrate, the better the quality. Songs deviating from Apple's standard (for example, CD-quality music or high bitrate MP3s) will use more disk space.
History
3. Nano's predecessor, the iPod Mini, was released on January 6, 2004, and was available with a 4 GB hard drive. The Nano was first released on September 7, 2005, and was the first iPod to use flash memory. It was first available in 2 GB and 4 GB versions. The fourth generation Nano was released on September 9, 2008.
Size
4. The fourth generation iPod Nano is 3.6" tall and 1.5" wide.
Video
5. The third generation Nano, released on September 5, 2007, was the first Nano to feature video playback. Storing videos on Nano can dramatically reduce the amount of songs it can hold.

Yamipod

I remember there be a 'copy to' function under File, and you had to 'select all' in edit. If you can't figure it out tell me or look in help files/faq's.

Press and hold the center button while holding down the menu button. This will reboot your Ipod. Check your IPod cable to see if its shorted. If might have transferred a song and crash in the middle of the transfer.

Make sure your headphones are working properly by testing with your computer headphone jack.

Is the headphone port on the Nano loose?

Connect the Nano to your iPod dock and see if you can head audio through the docks headphone jack.

If the headphones work, and you can get audio out of the dock headphone port, then there is a problem with your Nanos headphone jack.

The currently shipping iPod nano replaces the iPod mini. Both models use the "Clickwheel" (which places pressure sensitive navigation buttons underneath the scroll wheel) introduced with the iPod mini, but the similarities between the iPod mini and iPod nano end with the "Clickwheel". The iPod mini shipped in a colorful "ultra-portable (3.6 inch tall, 2.0 inch wide, 0.5 inch thick) lightweight anodized aluminum" case available in five stylish colors--silver, gold, pink, blue and green (four colors from February 23, 2005 to September 7, 2005 with gold no longer offered), each with a 1.67-inch "white backlit" monochrome LCD display. The iPod mini has either 4.0 GB or 6.0 GB hard drives to hold approximately 1,000 or 1,500 songs (encoded at 128-bit), respectively. The iPod nano, on the other hand, ships in a "impossibly small" 3.5 inch tall, 1.6 inch wide, and 0.27 inch thick "iBook white" or jet black and stainless steel case with a 1.5-inch "blue white backlit" 16-bit color LCD display. The iPod nano has either 2.0 GB or 4.0 GB of solid state Flash Memory and can hold approximately 500 or 1000 songs, respectively, in 128-Kbps AAC format and up to 25,000 "iPod nano-viewable" photographs

The iPod nano, introduced September 7, 2005, can hold approximately 500 or 1000 songs (on the 2.0 GB and 4.0 GB versions respectively in 128-Kbps AAC format) and as many as 25,000 "iPod nano-viewable" photographs.

The currently shipping iPod nano replaces the iPod mini. Both models use the "Clickwheel" (which places pressure sensitive navigation buttons underneath the scroll wheel) introduced with the iPod mini, but the similarities between the iPod mini and iPod nano end with the "Clickwheel". The iPod mini shipped in a colorful "ultra-portable (3.6 inch tall, 2.0 inch wide, 0.5 inch thick) lightweight anodized aluminum" case available in five stylish colors--silver, gold, pink, blue and green (four colors from February 23, 2005 to September 7, 2005 with gold no longer offered), each with a 1.67-inch "white backlit" monochrome LCD display. The iPod mini has either 4.0 GB or 6.0 GB hard drives to hold approximately 1,000 or 1,500 songs (encoded at 128-bit), respectively. The iPod nano, on the other hand, ships in a "impossibly small" 3.5 inch tall, 1.6 inch wide, and 0.27 inch thick "iBook white" or jet black and stainless steel case with a 1.5-inch "blue white backlit" 16-bit color LCD display. The iPod nano has either 2.0 GB or 4.0 GB of solid state Flash Memory and can hold approximately 500 or 1000 songs, respectively, in 128-Kbps AAC format and up to 25,000 "iPod nano-viewable" photographs

The currently shipping iPod nano replaces the iPod mini. Both models use the "Clickwheel" (which places pressure sensitive navigation buttons underneath the scroll wheel) introduced with the iPod mini, but the similarities between the iPod mini and iPod nano end with the "Clickwheel". The iPod mini shipped in a colorful "ultra-portable (3.6 inch tall, 2.0 inch wide, 0.5 inch thick) lightweight anodized aluminum" case available in five stylish colors--silver, gold, pink, blue and green (four colors from February 23, 2005 to September 7, 2005 with gold no longer offered), each with a 1.67-inch "white backlit" monochrome LCD display. The iPod mini has either 4.0 GB or 6.0 GB hard drives to hold approximately 1,000 or 1,500 songs (encoded at 128-bit), respectively. The iPod nano, on the other hand, ships in a "impossibly small" 3.5 inch tall, 1.6 inch wide, and 0.27 inch thick "iBook white" or jet black and stainless steel case with a 1.5-inch "blue white backlit" 16-bit color LCD display. The iPod nano has either 2.0 GB or 4.0 GB of solid state Flash Memory and can hold approximately 500 or 1000 songs, respectively, in 128-Kbps AAC format and up to 25,000 "iPod nano-viewable" photographs