Some of the older quests have a trend of issues that can lock an item away from you for the rest of the campaign. One character this affects the most is Grombrindal. He has several quests where you need to send an agent all across the old world which is fine enough. The issue arises when he needs to beat 2 Greenskin armies after you have finished them off if you pick Thorgrim as your starting LL. Or when you need to beat 2 Norscan armies which are so far away and possibly already stomped on by Bretonnia and/or the Empire. This issue affects Vlad to a lesser extent when he needs to capture that settlement north of Sylvania when Mannfred or Drycha took it. You're then forced to wait for something to happen like a confederation, the owner losing the settlement, or you just need to declare war on Drycha.
There are many quests from the older faction LLs that need a simple rework. I don't want them to be easier, I just don't want them to either take too many turns to complete or just impossible due of circumstance.
Some people would suggest using the Instant quest item/battle mod to circumvent this issue, but then I run into the issue that when I play Bretonnia that half of the items only have one quest and no battle. So when I reach the level the item is lost to the void from a buggy mod that's never updated.