FYI, Gorski and Superduper are fine. I've cleared both locations before Jammer's sent me there; in both cases, you just return to find yet more damn ghouls have moved in, and the quest seems to have no issues. Kill new ghouls in Gorski and quest completes; and in SDM you only need to find the item anyway.
(I think I once cleared Olivia before being sent there, but since it's a "new gang" residing in the place, it's fine. Dakka doesn't exist before the bounty appears, so I don't believe you'll actually hurt anything. Olivia is weird even without clearing it first; on different occasions, I have found one (1) hostile raider inside the place, standing next to Dakka, who attacked me immediately. Fortunately neither Dakka nor her gang reacted to my defending myself (tho Dakka *does* say her "I will kill whomever did this" line over the body, which was funny) - or sometimes you will find Dead Ack-Ack next to Live Ack-Ack. I have no idea why she'd be dead, but I'm guessing her SSC clone aggroed and killed her Vanilla version!)
(Side note - I would actually recommend clearing Olivia, personally, because Ack-Ack is a good source of early 5mm ammo =8) we can always pretend that Dakka's sidekick is someone else! Just remember not to pick up that locket, or it'll be in your inventory forever!)