I agree with tij. Making audio files by going digital to analog to digital is bound to reduce the audio quality. You can just set the play range using [Playback Range] for tracks to exclude silent portions at the beginning or end if you don't want them to play. Using the Duration of a track digitally ripped from a CD can make matching that track to find metadata much more accurate.
If you wanted to remove the silent sections at the beginning and end of the files completely, just;
1. Rip the CD digitially directly to FLAC.
2. Determine the start and end positions you want to use for actual playback, which can easily be seen using the spectrum analyser in the header, avoiding any lag in hearing the audio and reaction times.
3. Update the [Playback Range] tag to reflect that start and end positions, using the format "hh:mm:ss.xxx-hh:mm:ss.xxx", so to three decimals places of seconds. The [Duration] in MC will now reflect only the defined playback range.
4. Optionally use the Convert function to "convert" the FLAC file to FLAC, which will only convert the Playback Range you have defined, without any actual conversion. That would just trim the file.
Then you get no digital to analog to digital conversions, and you get a FLAC file that only includes the audio you want.
Your first image doesn't show any evidence that MC thinks there are 8 copies of the tracks. In fact, it doesn't show much at all, because it doesn't show the filename and path of the tracks, and you said you selected the Playlist Group and then searched for "smokie", but the image doesn't show the group that was selected or what is included in it. Basically, it looks like you have those tracks in multiple Playlists, and so your search for "Smokie" shows the multiple instances. Form a better search process and you will be able to confirm what you have there.
Finally, if you hit Printscreen Windows copied the screen image to the clipboard. If you had multiple files selected in MC, and tried to paste the image into Photoshop but still had MC in focus in Windows, then MC did exactly what you told it to do, and pasted the screenshot as Cover Art for the selected file.