My players had just left Vargas after he told them to investigate Fiona Wachter when them came across a very handsome well dressed Vasili Von Holtz. He greeted the party and Ireena and was eager to help them by showing them around town. I had them all make perception checks to notice Ireena blushing as she shook Vasili's hand. In my version Vasili looks exactly like Sergei, so Ireena is instantly drawn to him but does not know the true reason why. The party was like "aw how cute she has a crush, let's fix them up." (I found a handsome photo of sergei online to show the group and the ladies in the party immediately liked him.)

They asked about his wonderful clothes, and he told them he owns a tailors shop down the street, Vasili's Vestments. (I dislike the tax collector idea, tax collectors don't scream likeable to me... sorry H&R block people). After taking them to his shop he gave them all brand new fancy clothes, free of charge. "Women as beautiful as yourselves wearing my clothes is excellent advertising." (Minus the one male barbarian in the group the rest are ladies)

After, he offered to show Ireena to the church, where she had been asking to go but the party had other quests they wanted to do (investigate lady wachter, find their ally the man with the monkey, see this blinksy dude they've heard about, investigate the orphanage) so they sent Ireena off on her own with Vasili.

Later they caught up with them at the church, Vasili was inside (I had the bones be missing but Lucian hasn't found out yet). Ireena said she was safe at the church and she didn't think she should involve herself in their political espionage quest, due to her status. I also may have jumped the gun and told them the gravedigger hasn't come to work for the past few days, so they'll be investigating the orphanage without first learning about the bones. Vasili offered to check in on her when he can, and took the party back to his shop to talk in private. He told them the Baron was not a man to be trusted, and lady Wachter was not as bad as she was made out to be. He emphasized the cruelty of Vargas and how his father was even worse. He made sure to downplay the threat of Strahd, saying he hasn't been in Vallaki for over 100 years (oh the irony) and that he's not even sure why Strahd would want to destroy Vallaki anyway (technically true, Strahd enjoys a city of abundent fresh meat so close to home). And with that he sent them on their way to meet Fiona Wachter, who will next session ask for help in bringing down Vargas.