I think the biggest advantage to nitrogen is that it doesn't change pressure as much as air in response to tire temperature. I believe this is why the military likes it for aircraft tires (as do civilian airlines) - because those tires go from as low as -40 or -50° at altitude to smoking hot at touchdown, and minimizing thermal expansion/contraction and the associated extreme pressure changes associated with oxygenated air is critical for tire longevity and aircraft safety.
As regards nitrogen's molecule being larger than oxygen's and thus having greater resistance to leaking directly through the tube wall, the air around us is already ~78% nitrogen - if leakage through the tube walls is the sole source of pressure drops, a few top offs should mean one is soon approaching 100% nitrogen as what's leaking out is the oxygen. That said, I would personally put nitrogen in my tires if it were ready available, but I wouldn't pay extra for it.
Edit: Changed "air pressure" to "tire temperature." Good catch Mr. Westman. I try to proofread, but I always think I wrote what I thought I wrote.