>Would 2 wooden belt buckles give as much prestige as 2 Nisha shortbows if they are both asked for when asking for a hard work order?

There's two types of difficulties that factor into prestige. The one you ask for (hard, challenging, etc), and the objective difficulty of the piece to make.

Yes, this means a more skilled crafter can gain prestige faster given the same amount of items turned in.

---

Weapons for Sale:
https://elanthipedia.play.net/mediawiki/index.php/User:CARAAMON#Wares
Hunta Talna Kortok, built by Gor'Togs, for Gor'Togs
http://www.angelfire.com/rpg2/caraamon/home.html

They are both the same difficulty level. So in terms of prestige, both will give the same amount. (assuming you take either as 'hard' and the same amount of product to be made)