[SixOfSpades]

I've only done the Ranger Stronghold once, and chose to take the safe route and not to supply the Imnesvale Three.

However, once thing I've noticed in my non-Ranger games is:
1) If you give them their swords & ale, and later on (before you kill the Shade Lord) you visit the Inn and talk to people, you'll find out that a couple of parent-type figures are mad about what you did to contribute to the delinquency of minors.
2) If you then beat the Shade Lord and re-explore the Umar Cave, you can go back to the parents--and they're pleased as punch at what you've done to help give their kids a Life Lesson.

Theoretically, it shouldn't matter what class you are, or what course you take with the boys, as long as you complete it before you talk to the mayor and get your stronghold. That way, even if giving the boys their swords and ale meant that you LOST the Cabin, then talking to the Mayor means you get it right back again.

Personally, I see nothing wrong with giving the boys swords & ale. I myself have "barely fuzz on my chin," but I'm certainly able to handle a weapon without accidentally inflicting bodily harm to anyone, and I'm over legal drinking age anywhere on the planet.