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Case 2: OBS + Desktop Audio source
You are into Case 2 if:
You use Windows with an audio software and MME/DirectX drivers, with or without external sound card.
It is as simple as case 1 but with a little variation.
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Open your audio software, make it play some sounds, and remember the audio output it's using
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Open OBS and go to its Preferences (Settings panel), then into the Audio tab.
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In the Devices / Desktop Audio drop-down list select the same output as your audio software.
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Click OK then in the OBS audio mixer you should see the VU-meter of the "Desktop Audio" source moving relatively to the sound your audio software is outputting. Sometimes it seems a big buggy and you need to click the gear ⚙️ of the Desktop Audio source, click Properties, then re-select the same output you just selected in the previous step. You can also try restarting OBS (don't worry, it will automatically save your session).
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Awesome, you are now ready to go to part 3!