Board Thread:General Discussion/@comment-25266931-20170224140119/@comment-10380701-20170228061156

Thing is, both Qrow and Winter are both stuck in their fighting style. This applies to most Huntsmen, outside of major upgrades to their weapons.

Literally Weiss' reasoning for the creation of Myrtenaster was to one up Winter, who can only use two Dust types for her swords.

Older is better in this case because Qrow has more time doing what he's doing for a while now. If we're talking about a different profession then Qrow might be shit out of luck given his age. While it does have limitations once you reach a certain age, this trope remains true for quite a while.

And even by the time you pass the threshold for being an old person, by that time, you have so much battle experience you can hone the next generation to do better.

Which, given Qrow's already mentioned experience, means he's about to reach the point where he becomes the mentor archetype to RWBY and JNR.

As a non-main character, it's his role in the story to get the main character to get better, as he's at the peak of his strength and it's only downhill from there while the main cast still has room to grow.