Valentino is so cute and I love the name!
As for the drink price, you need high level mixology and the Marketable reward to get the high values.
To get Lilith to drink a cure, you need to make a group serving (make drinks for everyone or something like that). Add Lilith to a group with Caleb and “grab drink together.” You should be able to cancel it in Caleb’s queue and Lilith should still grab hers. The group serving costs the same and uses the same ingredients as a single drink.
Alternately, if the relationship is high enough, you can do it as a friendly social. Have the drink in either Caleb’s or redhaired Lilith’s inventory and “offer to cure” should come up. I don’t remember what the friendship cutoff point is, but I used that for a spouse in my Ten-Gen Townie Dynasty. Basically, keep doing friendly socials until you get the option.
