During my first run of D&D a couple years ago I was running with a Lawful Neutral character.
Because
"I am! THE LAW!"
It was actually enjoyable since I was a "Judge" like character. It allowed me to bend the rules a bit more when compared to other classes. I remember a run in with a merchant where my character was poisoned. Generally in the game (This DM's setup) an antidote was 250 I believe, the merchant was trying to charge my character 3x as much. So instead of paying, I had the other PC I was with distract the merchant by just talking to him and asking questions. In the mean time I stepped around to the back of the wagon, picked a few locks then made off into the forest with a handful of fist sized rubies, the antidote and an enchanted Armor with melding on it. A single tap on it and it would appear however I wanted it to look. All because a merchant tried to charge me more in my time of need.
More recently though I've been wanting to pick D&D up again.
Maybe try a Neutral Merchant character with no real stance.