Its really hard to compare the reliability of the two. Two very mildly tuned engines, I would say the four stroke will last longer. The higher the state of tune gets, the more I lean towards the two stroke because of less moving parts so less things to wear out when pushed to the limit.
Another thing is for a given CC the two stroke makes more power all over, most people don't know that. Most people don't know that two strokes make strong bottom end torque because they are usually tuned to keep up with four strokes twice their size, which means they are in a very high state of tune and all of their power is in the top end to match peak power numbers.
A large mild two stroke is a wondrous thing we rarely get to buy. For example, a 450 single. A 4 stroke 450 single making 55 hp is a high strung, unreliable, heavy, expensive, slug. A 450 2 stroke single, if tuned to make the same peak power, would be a light weight, extremely reliable, torque monster that would go twice as long between rebuilds and cost 1/4 as much to maintain.
A lot of people who have never ridden a KX500 or CR500 imagine them to have the same kind of powerband as a 250, only twice as much. Not so. They really don't make all that much more power than a 250, definitely not twice as much. They have stump pulling torque and lots of reliability. Since they aren't in a class competing against four strokes twice their size, they made them all around good engines instead of going for peak power.