I'm playing a merchant character in a stealth/heist/social game. I'm using the rouge archetypes fence and guild agent. So I'm curious what magic items I should invest into, or any other recommended things. We're starting at level 5 and I plan on taking the leadership feat. All Paizo content is allowed, and third party stuff can be used, though it's up to a vote.
Right off the top of my head I'm thinking a Hat of Disguise and/or Headband of Charisma. A Bag of Holding goes without saying as well.
You'll want a handy haversack or a minor bag of holding and/or a pathfinder pouch, certainly. A hat of disguise might also fit, and a runeward tattoo (illusion) might be appropriate.
Despite the setting I'd still consider a weapon, headband or belt of your favourite abilities & a cloak of resistance.
Knight's Pennon of Parley (4,500 gp):
The white knight’s pennon of parley, when displayed approaching a negotiation, grants the bearer a +4 enhancement bonus on Bluff, Diplomacy, Intimidate, and Sense Motive checks for 1 hour, so long as the bearer does not initiate any hostile action.
Eastern Star Ioun Stone (4,000 gp):
Its user understands spoken and written languages as if under the effects of comprehend languages.
Glittering Trinket (120 gp):
Though actually made of cheap tin and colored glass, this adornment appears to be a beautiful and expensive piece of jewelry worth 1,000 gp. A glittering trinket can come in the form of a necklace (using the neck item slot), a bracelet (taking up the wrists slot), a belt buckle (taking the waist slot), or a ring (taking up one ring slot). The trinket’s inflated price affects only people’s opinion of the wearer. It uses its actual price and cost for any abilities or effects that depend on the item having a certain value. Anyone who physically interacts with a glittering trinket can attempt a DC 11 Will save to disbelieve the illusion, and a successful DC 20 Appraise check identifies it as false. Because of these factors, selling the trinket—especially to a merchant—rarely fetches the inflated price.[/i]
/cevah
Ring of the Sophisticate
For that small boost to Sense Motive and to find the keys after a pub crawl.
Bracelet of Bargaining
To seal the deal!
Black Marketeer's Bag
It's a Handy Haversack for shady dealers
Deck of Doors
For when the deal goes wrong
Ink of Mimicry
A great tool for any urban/intrigue setting
In all honesty, I wouldn't spend a ton (perhaps not even any) on 'merchant' type stuff. Against most people, you will have enough skill to dominate negotiations anyway, so more won't help much. Anyone who is a serious opponent will probably take steps to ensure that they are not influenced by magic, so against them it won't help.
I expect that even in a stealth/heist/social game there are going to be times when you will end up in more traditional combat style situations, which I expect you are not very good at. Using your wealth to shore up this weakness and give you options seems like a better plan to me.
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5th level, starting with 10,500gp?
While you don't want to rule out combat items, you can certainly treat them as lower priority. For example, I wouldn't bother with a magic weapon - masterwork will do.
A Cloak of Resistance and Belt of Dex are useful in and out of combat (especially with a finesse build), so I'd suggest spending half of your wealth on a Cloak +1 and Belt +2. Add your masterwork weapon and decent armour (maybe +1, or a mithral shirt) and you should be set for combat. That leaves you 4-5K for utility and intrigue items.
Handy Haversack (2k) and Pathfinder Pouch (1k) are good picks. Black Marketeer's Bag (pouch security, haversack capacity) is too pricey just yet at 6.2k, but you'll probably want one soon. If you haven't entirely dumped Strength you can probably grab the Pouch for now and upgrade to the Bag in a level or two.
Sleeves of Many Garments (0.2k) are a cheap way to change your clothes, which could help you switch social settings or assist in a disguise. For a bit more gold, the Hat of Disguise (1.8k). Glamered Armour (+2.7K) is probably also worth it in the long run - check with your GM about the social reaction to light armour to decide how to prioritize it.
I don't think there's much of a magical defense against an item that increases your skill modifier, unless it's an item that increases the opposed skill (eg defending against a +5 Bluff from a Bracelet of Bargaining with your own +5 Sense Motive from a Bracelet of Bargaining). So you'll probably want one or more skill-boosting items eventually - and I'll add Circlet of Persuasion (4.5k) to the list of possibilities.
Don't forget mundane gear. I'd invest in at minimum a courtier's outfit and accessories (80gp total), as well - maybe even a noble's outfit. Alchemist's Kindness (1gp/dose), a Grooming Kit (1gp), and Perfume (1gp+/dose) are also fun for flavour. If you didn't get the Pathfinder Pouch, Hollow-Heeled Boots (10gp) are a cheap smuggling boost. You might also find use for invisible ink (2-75gp/vial)
I might come up with a few more things later...
The runeward tattoo (illusion) I suggested is for exactly that purpose EM.
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Link to illusion runeward tattoo - it would allow you to detect illusions at will for 1K and no item slot. In fact, it automatically alerts you when illusions are cast within 60ft, which sounds handy.
Other options I can find are a Lantern of Auras (2k), or a Cloak of the Hedge Wizard, Divination variant (2.5k).
Or you could take the Minor Magic rogue talent - not sure how that stacks up against your other talent options.
Chest of the Mercane for ordering specialty items on request and selling them at a markup, or for fencing stuff they "acquired" and are having trouble unloading.
At the price, though, it's something to build up to rather than start with. Alternately, make friends with a mercane.