Kelteel,
Regarding the second upgrade, you can do it right after the first upgrade (when you're speaking w/ Sassan about upgrading your workshop). You have the options of upgrading armor, weapons, or jewelery enchantments. After you make your first choice, you can tell Sassan that you want to upgrade your workshop [again]-- you're given the options again. I've chosen to upgrade weapons and armor, I think-- I don't know if you can "double upgrade" a single thing (say, upgrade weapons twice), but I'd assume so with the options being available.
Hope that helps you!
~~CierraShore
