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So I've now cleared the rest of Caria Manor and the surrounding lands. The Red Wolf is much more difficult on a field compared to inside a Debate Hall. I've also entered Lady Ranni's service and have now descended down the Siofra Well to meet with Blaidd.
Additionally, I have tried to craft my own "Elden Bling" as it were while still trying to keep my gearset balanced:
Bandit Mask
High Page Clothes
Banished Knight Gauntlets
Banished Knight Greaves
The weapons I change frequently