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Is there a problem leaving the TrackClip Pro plugged in? I use it every other day or so and unplug it if it's going to be much longer. Are there issues leaving it plugged in essentially all the time?

Yes and no, theoretically the LEDs can burn out, however this would likely take years. If you leave it plugged in for a day or 10 here and there it's not a big issue in the long run. If you're really concerned, something like this may come in handy.