It is very possible the problem is on his end, not yours.
One interesting way to "listen to yourself" is to use WebSDR (). Find an open SDR with an appropriate freq range and antenna, tune it to where you'll transmit and listen (or record) while you send. Of course, you can always call a friend to listen as well ... but that is less techy :)
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-Mat Breton, N8TW
Mat Breton N8TW