Cons

Potent Potables (apothecary)

I would like to use disguise to dress as a rich elderly wizard, who lackadaisically selects a few choice items from a apothecary. I would get a couple of potions, alchemist fire and a magnifying glass. Upon going to the counter, I will charm the owner (provided he is not an elf.) Then I would talk him up a bit. I would then pull out a bag of copper coins that I have changed with prestidigitation to look and smell like gold. 

If he is none the wiser and too happy to see his old friend then I will pay him with the 200 "gold" coins and move along. 

If somehow knows it is not gold, I'll feign outrage saying that a client of mine payed me with that. Then I would tell him that I must go denounce this person. On my way out, I'll filch a couple of small items with Sleight of Hand. 

If he wants to detain me, I'll cast fog cloud and head out the door pretending there was a chemical explosion. I'll get lost in the crowd and cast disguise self to blend in as an elder lady. 

I also want to have my raven try to steal 'shinny things" whenever he can safely do so.

Downtime Used: 1 (Cost to setup Con = 4gp)

Result (1d100+3=19): You regain consciousness in the woods 3 miles from where you last remember being, with no memory of how you got there. You are naked and armed only with a wooden spear hastily carved from a sapling. You have been robbed of 45 gp.

Attempted Disguise (Disguise 1d20+3=17 [DC 15]): Success (Kelner failed to be able to accurately describe you to guard)

Description: The owner of Potent Potables, a friendly-talkative gnome named Kelner, is excited at the prospect of making a sale. Sangrux mystic charm draws Kelnor into a spirited conversation about potions. Later, after Sangrux has left, Kelnor exclaims in surprise, realizing that the coins have been disguised magically. Heading home from his con, Sangrux realizes he is being followed. A quick fog cloud and vanishing into the crowd appears to work wonderfully, until he feels a brief prick of pain.. followed by a loss of consciousness. Sangrux wakes up in the middle of the woods, a few miles out of town, with all of his belongings stolen. Luckily, Sangrux kept his spellbook and a stash of coin at home and he is able to re-purchase his belongings, although it puts a serious dent in his coin.

Matteo’s (weaponsmith)

I want to then do the same with an armory so that I can buy a special/enchanted padded suit and whip, if possible. I'll dress as a sailor that has just completed a voyage and do the same thing. Charmed, changed coins, etc. If any guards detain me, I'll tell the guards that I am on official business from the king and that I cannot be stopped at this time. Then I will show them my credentials as a special investigator from the king. If they interfere, they are messing with official business. 

Downtime Used: 1 (Cost to setup Con = 4gp)

Result (1d100+3=32): You are caught up in a whirlwind romance that is ongoing with a priestess of Loviator, Zellani (your new love interest might represent a new bond). You wake up in a sumptuous bed in the temple. You are holding a whip. A young half-elf male is asleep suspended from the ceiling by leather straps and Zellani is curled up by your side.

Attempted Diguise (Disguise 1d20+3=22 [DC 15]): Success (Matteo is unable to describe the sailor well enough to locate him)

Description: The owner of Matteo's, a towering serious half-moon elf, listens thoughtfully to Sangrux's desires. He agrees to sell him a set of leather armor that can change appearance at will. In additional he sells him a whip that coils by itself and can channel magical energy through it. Unfortunately, he charges half up front and the sum is far more than Sangrux has. Thanking him for his time, Sangrux decides to woo Zellani in the hopes of getting access to a wealthy patron. The heated evening leaves him tangled in Zellanis sheets the next morning, wondering exactly what transpired the night before.