Make an OCR bump of 5-10 for a failed pickpocket attempt on one of these bad boys and the problem will sort itself out.
Also you exaggerated a fair bit on some of your numbers unless this has somehow gotten WAY more lucrative from when I used to do it. What's your appraise at to make each necklace go for 1,000gp? I used to have a character who HAD appraise, and the 2 rings, a necklace, a torch, and a cloak with appraise on it and still didn't get that much at Mist Camp or Blaustein.
I hoped back on Nicoletta to see what she used before selling her stuff. Go ahead and give this a try and report back with what you get.
Innate appraise: 3 (I swore I had more. It might be because I'm in ghost form)
Innate influence: -2
Silk clothes: +3 influence
Performance boots: +4 influence
Ring of lies x2: +8 influence
Amulet of Souek: +5 appraise
Merchant gloves: +4 appraise
Knightly cloak: +1 influence
Golden belt: +2 influence
Perfume offhand: +5 influence
I suspect since you play a vardo captain you'll have more influence/appraise flogging these things at Blaustein. You can go ahead and take screenshots showing what the actual prices are to correct me. If Nico was alive, I'd do it myself.
Even by the conservative estimate, 400 gp, that's still 5600 gp a suitcase. Perhaps an accurate representation would be a rogue with just appraise/influence gear and no skills whatsoever in appraise flogging this at blaustein.
your spirit animal is a snark emoticon, Legion.
If you're caught in the Bluewater, you get attacked by garda and are in a world of hurt. And if a DM is watching they'll have a garda report filed, since NPCs noticed you and would report it.
You can skip the blue water and only miss out on two necklaces. If you have any chance of getting caught you could just skip and have plenty of room to run off in the sewers in the streets of Vallaki.
If you did get caught in the blue water though, definitely in trouble. I don't know how many people try this when they have less than 20 pp personally.