I have played a rogue so often in games that, at this point, I refuse to take any rogue skills on my character sheet: I can hide and sneak and steal and beat-feet with the best of them.
I end up having to give a lesson on being a thief/rogue that people don’t hate A LOT.
The biggest problem with being a successful rogue is that you are doing things that are going to make people mad. You are going to be thieving and lying on a regular basis.
Sadly, this tends to make you enemies. Having enemies IN-GAME is a good thing. Having enemies OUT-OF-GAME is a bad thing.
You want to avoid being a dick. I am sorry for the frank language, but it is true.
You are going to lie as a rogue. It just happens…
Don’t mistake being a rogue with HAVING TO LIE. You CAN tell the truth and still be in-character.
Be smart. Does it actually do anything for you to lie about where the main villain went? Then don’t do it.
Unless you can actually make bank or have a real reason to have to lie, don’t do it habitually if you want to be a successful rogue. People won’t ever believe you, and then how can you get them to look in the wrong place for the Treasure Of MasterGoldEnStien?
(Being a habitual liar for BAD reasons is an entirely different character concept.)
If you are going to steal, NEVER STEAL EVERYTHING. This is a HUGE rule. Yes, I know that your character would probably steal everything that is not nailed down, but then you are going to make out-of-game enemies.
There is psychology behind this that may make so called “role-play purists” mad, but if you think that no one is going to be mad at you for stealing their shit, you need to go home. Understand that people spend a lot of time gathering up their money, components, items, etc. If you take all of it, they will become disheartened, angry with you, and may even not want to play anymore.
You can still steal things! But you have to use good judgment so that you can be a successful thief without making players mad, or being a jerk.
Here are some good rules of thumb:
Only ever steal (at most) 10% of what people have. If they have 10 gold, steal one. This means you have more money, and they can’t really be too angry. It’s only one gold!
If you see a bunch of items that someone has, never steal their coolest, best item. They probably spent a lot of time getting that, and it will dishearten them Out-of-Game if you take it.
Yes, I understand that your character would take it, and I know that you think that they are bad role-players if they get upset, but you are wrong. You, not your character, are being mean if you take someone’s favorite toy. Take something else! If you see a Staff of Blasting, a Pendant of Dodge, and The High Gift Of The Gods To Magey McMageinstine: take the staff or the pendant. Leave them their awesome toy, so that they don’t get mad at you out-of-game.
You want to be a rogue who can thieve and such, and you can! Just make sure that you don’t alienate the other players at the game. Get yourself a reputation as a good rogue, but also as an awesome player.