Are you transmitting AM or CW [of FM]?
You can listen to AM with a simple diode detector but the levels will be critical, too low and the recovered audio will be too weak, too strong and the audio distorted.
Is there a local ham you can talk to via telephone while he monitors your audio?
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As to coupling a PC to a transceiver, yes it can be done, transformers are good for breaking ground loops but bad for picking up stray magnetic shields.
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These show several ways to do it.
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Mr. Browne knows hit stuff, both RF and AF. He was a respected audio expert for ~40 years before retirement.
I use transformers but they are obscenely expensive units with integral faraday cage, electrostatic shield between primary and secondary.?
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Jensen makes similar transformers (prepare to rob a bank). I salvaged the transformers from an audio distribution amp designed back when we (professionals) used 600 ohms for everything audio, then we went with 10K loads and the old distribution systems were tossed.
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Rod Elliot shows two circuits that can modified to drive a transceiver,
one for transmitting one for receiving
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The PC to PA can be modified for PC AF out? to transceiver AF in
The PA to PC can be modified for transceiver AF out to PC AF line in.
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If you are lucky, in a location or ham shack with no stray electromagnetic fields, Mr. Elliot's designs should work fine.
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