Might not be rolling in it so much. If he's 27 and in the Reserves, he sure didn't come off AD. I did 8 years AD, then 15 in Reserves, but 90% of my retirement points were earned in those first 8.

The Guard/Reserve guys who never did AD usually figure out around the 10-12 year point how small the retirement check will be, that they won't see it until 60, and that if they get activated for a couple years will never make up the loss of income. That's when they punch. And that's also about the point you don't fly much, just get fitted for a large steel desk.

Side note in the "insult to injury" zone: Most Guard/Res guys are clueless that their "inactive duty" points are capped each year. Pay only, no point towards retirement. I retired with over 3 years worth of points that didn't count.