Should I go out with him?

A few months a guy, I grew up with, contacted me and over time we have caught up. We were friends (not super close though) from elementary school through high school. After talking for about a week I found out that he was going to be deployed and that he has a five year contract with the Navy (it will be up in 2017, the year after I graduate college). He asked if I would write him letters while he is away and so we have stayed in contact. Recently I learned that he likes me and wants to see where things go; so when we are both back in the country he is planning on teaching me how to snow board and hanging out a bit.
I have promised myself that I would never be in a relationship with someone in the military due to the emotional strain, but he is not planning on staying in so I don't have much of a problem with that. However I am very nervous because after being in the military he wants to become a helicopter pilot. I don't know whether I should wait it out and let myself continue to get to know him or if maybe I should wait for someone else with a life plan that feels a little more stable and save my emotions. I worry that as a pilot he wont have time to be around much. I seem to always find a reason not to date people though and I am not sure if I am being rational. Should I give him a chance? What is it like to date a pilot?