I'm a 1st time user and the install went well on my Win10Pro laptop. Next I selected a prepared folder of music and clicked "+ADD" for about 900 mb of files to be added to my old iPod Shuffle 2nd gen. After seeing the files added to the program windows very quickly (too quickly in my experience to have been a real copy of the files to the iPod), there was no confirmation of completion. Suspecting files hadn't in fact been copied, I went to the iPod folder and saw no files on drive. So, the "+ADD" button is only for selecting files, not selecting and copying, as some programs of this type might do. With the "UPDATE" button far to the left, it appears disconnected to the add/copy function. Normally, logic for a program process "update" in this case is for rescanning a device to look for changes, not APPLYING them. I think this should be clarified by a message like: "Your files have all been selected. Click UPDATE to copy those files to the device", or some other assist to the user as to where we are in the process.
2nd item: once I figured out the update issue, the progress bar(s) began working. However, the window showed no changes or indicated what files were being or had been worked on. A common way of doing this is for the file in process to be highlighted, the file to be named, a blinker next to the file or some other indication or combination of them. Further, files that have been completed often change to another color, either by font color change or by a line highlight that stays activated though the rest of the copy process. EAC's (Exact Audio Copy) progress indicator is a good example of this. I haven't yet uncovered a setting to do this. Further, if the user wished for some reason to terminate the process early (time crunch, change of mind about the playlist, etc....), this would allow some idea of what had been done if a specific minimum work was desired without restarting the whole process and/or wasting more time. I hope you will allow this feature to add more transparency to the workings of the program.