There are some good options for a Sandpoint native. You could use an orphan holed up in the Turandarok academy (perhaps they were siblings, etc). You could treacherously use Ameiko Kaijitsu... when she's kidnapped by her brother, it will highlight the danger of the drawback.
For outsiders, there are other options. If the character is from a rural family, you could dramatically play up someone from the Turtleback Ferry area, or one of the farmers who are threatened by ghouls in the Skinsaw murders.
As per objects, it can be something as simple as a razor or a hat. If the character is the object of the Skinsaw Man's obsession, and personal effects start to go missing, I imagine that the attachment will be accentuated (even if the object in question never goes missing itself).
The attached drawback is always situational. :) You don't want to overuse it. Objects are the best if you want to inflict the drawback more often, since it can be affected with things like sunder (broken or damaged, must be fixed) or theft. Nothing stops something stolen by the Skinsaw man from being interacted with in other ways after the fact, either.
You could bring along a person who is the target of an attachment, even to dungeon crawls. I wouldn't, in your place, because I prefer to
a) have neat combat situations with a minimum of NPC mess
b) make threats more dramatic by having them appear occasionally, rather than regularly.
If your party is the sort that interact nicely, you could even discuss the possibility of having the drawback apply to another PC. That could make roleplay interesting in an otherwise unusual way, and add a little bit to some combats.
I must admit, I'd be tempted to put the attachment to a particular building in Sandpoint, if the PC happened to be a native. :) The opening sequence of goblin attack could be made dramatic when the little snots lit it on fire. Ghouls, dragons, and/or stone giants could also threaten the place in certain instances. Scarnetti or someone that the PCs don't interact with in a positive way could buy it. Lots of ugly possibilities.
