Unfinished business: Gil doesn’t really intend to go back to Rose’s house any time soon. It’s fairly dangerous, though he’s in a much better state to handle it now than he was back then. Of course, he’s just married into the family so it’s entirely possible that the system will demand that he reclaim Rose’s property and the Durst Family name. Lord Gilbert Durst has a nice ring to it, no?
Track down a crazy old bag with full intention of killing, capturing, or…. Ok, not fucking her. Gil’s penis would shrivel and die if it got anywhere near Baba Lysaga without her getting a serious makeover. She’s in the top 5 strongest spellcasters in Barovia, but thankfully not in the same weight class as Baba Yaga. Succeed, and Gil gets another binding.
Come to the aid of a secret Society of wereravens that quietly oppose strahd. This is probably the Singel group of people most likely to provide deal with actual material assistance without needing to be captured, strongarmed or manipulated, as long as Gil is a Goodguy.
Be extremely nosy with regards to local Noble families, uncovering, extremely embarrassing, potentially dangerous secrets. This may bring Gil into contact with one of the three great treasures of Ravenloft, an item of moderate power on its own and an objective of his Arc mission.
Do a fairly substantial favor for a faction which serves Strahd von Zarovich: The vistani. They are a group of nomadic fortune tellers, entertainers, peddlers, thieves, and assassins with an aesthetic you may find familiar. Their loyalty is not absolute and they’re probably the single best source of information that Gill is likely to find for basically anything in Barovia, and perhaps beyond.
A fuck Mary kill style mission that will bring Gil in contact with all three of the prior mentioned factions and will have potential to give him substantial rewards. Only problem? He will definitely need to choose at least one of the three to kill or get killed. Let’s get stuck in balls deep.
Save Gertruda, a damsel in distress, from Strahd’s castle. This is the option that will bring Gill into the most direct conflict with Strahd, as she is mesmerized and getting railed by the Count as we speak, but would also offer the largest quest rewards. The girl herself is… well she’s hot but she’s also a nearly 50 year old meme of a character originally designed to troll heroic player characters in the 80s. Think Snow, but without the shroud of super-luck and in a gothic horror setting. Of course, people in modern day keep reimagining her…
Use the recast item to create an entirely new character to take heat off of Ireena. Due to narrative resonance, putting Shiho into the role of Strahd’s obsession makes other characters from the Persona 5 cast appear as well, effectively creating a DND adventuring party that will draw some attention from Strahd that would otherwise go only to Gil.