playing sound files into telephone

I use a headset on my telephone connected by a coupler in the handset cord. The coupler also has a miniplug which I have connected to a tape recorder so I can play tapes during calls and both parties can hear the tape. I want to convert all of the tapes to files on my computer and play them from the computer instead, using an output from the computer sound card. The tape recorder output is marked with a little icon of a telephone, and I don't have any specifications on what is actually being output. The sound card has both a "line out" and a "headphone" jack. Would either of these damage the telephone, and if not which would be the correct one to use?

I would also appreciate any recommendations anyone might have on the best way to store the files and select them for playing as needed. I was thinking of storing them as .wav files and using Excel to link to them with a little macro to play the file when I select it.

Thanks in advance for any advice.

David

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David
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