If you were going to prison for more than a decade and were able to enlist in the military for high risk situations but half the time would you?

No I wouldn't. If I faced a long prison sentence I would cut to the chase and end my life. The military does accept some people who are given the choice to join instead of serve prison time. Like a last chance for them. For me I don't like the idea of having criminals forced to fight for a country. Gives too much opportunity for undesirable activities. Criminals can't be trusted especially when you bunch them all together and give them weapons.