Does running with music make it easier?
Music CAN make running feel a little easier, as you potentially may not be 100% focused on the exercise itself and thus don't think about how knackered you may be. Music makes you happy…(as long as you're listening to music that makes you happy), so if you're happy it can help get you into an optimal mindset.
What do Elite athletes do?
In general serious athletes or elite athletes tend to focus on internal cues such as breathing, heart rate, and muscular tension. So do not necessarily take as much benefit from an external factor like music. For other music can be a motivator & will help distract them from boredom that may occur when running. Saying that, many non-elite runners enjoy running without music & enjoy the same benefits. You don't have to be an elite athlete to be in tune with your body. And I know plenty of elite runners who run with music. GB 2012 1500m Olympian Ross Murray listens to music on all his easy runs.
When do we 'unplug' if we are always connected?
I think that the ability to unplug is something we are starting to lose in this day and age. With my work & lifestyle I spend a lot of my time attached to a computer. So getting out for a run is a godsend & I don't need music at all. It could be said that listening to music while running is multitasking, which we do all the time and prevents us from enjoying the running experience.
I personally think that listening to music on the treadmill is better than using it outside. When you run outside there are so many distractions with the changing landscapes, traffic, people and these external factor can provide a distraction and stop boredom. When you run on the treadmill you don't have these factors so I think it's nice to have something to keep you mulling over.
Should you race with music?
In general it's all down to personal preference. However, I'd say the benefits of running with music will come when you are doing easy running. Using music during sessions isn't ideal. But if you really need to use it every time you run then you can become desensitised to it so it wouldn't end up making a difference. Just make sure the races you enter allow you to use music during the race because you may end up relying on it.