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I would load it with 6 hours, to account for any songs that get skipped over.
It's always better to have too much and need to cut stuff, than to have too little and scramble to find something for filler! An hour of music equates to roughly a CD's worth of songs, about 15-20, so I would have an extra hour or two of music over whatever you need, or an extra 40ish songs.
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Due to some restrictions at our venue our only option for music is to bring an IPOD. We are paying for a sound system and tech to run it but I need to load it up with music. How much music should I put on it? We are having an hour for cocktails and then 4 hour reception. Thanks!