I looked for a 'how to' guide for thievery in DnD but have not found anything. Maybe you can help me decide which skills are most important to give the expertise bonus to at lvl 1?
If I wanted to build a thief centered around stealing and hoarding as much gold and magic trinkets as possible what kind of build should I be going for. Setting aside all Combat related stuff, I know I would want to gain expertise in a few key skills.
-Is deception more valuable than persuasion?
-Do I really need to max out stealth?
-Is slight of hand only for picking someones purse?
-Are Thieves tools usefull outside of dungeons?
Also which background would be best. I would think criminal. but the Sailor Variant (Pirate) looks usefull, as well as Entertainer if I can make gold with its feature.
http://community.wizards.com/forum/player-help/threads/4147321
http://community.wizards.com/forum/player-help/threads/4149876
So Cold In Here. I would have gotten a better discussion from an ATM.
I've seen both of those, and neighter of those threads goes into detail on stealing and the best way to do it.
As stated above, it all depends on what kind of "thief" you see yourself as. A cat burglar will have a high Wisdom and Expertise in Perception, Stealth, and Thieves' Tools. For a con artist high Charisma, but also a decent Wisdom, is needed. Also, consider magic as a means for augmenting your skill set. There's little that you can accomplish naturally that you can't replicate with some magic.
I think the biggest factor in your character concept is how it fits in your game. Is your DM going to ignore the rest of the party while he takes you on a nighttime burglary? I'd suggest talking to them on how they'd handle situations like this before you make your character.
Pandaemonius wrote:
If you plan on using stealth anything less than max is hurtful. While at low levels passive perception might be low, active perception is not because of the large range of the d20. Nothing hurts you more than trying to stealth and being spotted. If you fail a lock pick, you can try again (depending on the DM) or kick it down, or try something else.
Since stealth works irks differently in 5e than other editions, imho, it's something that you max out always. It could be the difference between successfully scouting an area or being killed while the rest of your party waits further back for your report.
Well damn! I didnt know bards could be better thieves than thieves. Thats an interesting concept. Things that I would miss not taking Rogue levels:
Thieves Cant, Reliable Talent, Second Story-work, and Supreme Sneak, Blindsense.
Things I Gain: Jack of all Trades, Cutting Words. Peerless Skill.
Im not sure how much I need Reliable Talent if I get Peerless Skill. But I would miss Thieves Cant too much, and the Jump bonus from Second Story-work is too awesome for me to give up being a cat-burgler and all. I think the Best option would be Rogue-Thief 3, Bard 17.
Maxing Stealth really is a conundrum. I did mention that Combat is not a huge factor in making decisions for me. I want to get rich quick by stealing as much stuff as possible. Being Stealthy around City Dwellers, Merchants and Nobles might not require Expertise, and could be wasted. Where there might be more value in giving Expertise to Forge Document or Disguise.
Wait, is it even possible to have expertise in something like forge document???
Yunru wrote:
Forgery and Deception can only go so far.
That said, you want Charlatan's feature, regardless of the rest of your background (see: custom backgrounds).
Yunru wrote:
I'm still a bit confused by your motivations. Is thievery the focal point of this campaign? If not, then you'd have to ask... why is it so important? Being a solid adventurer should net you far more coin then petty theft. If you're talking about something more complicated than petty theft, or something that could be adjudicated by a few rolls, then it seems that it would derail the session. Being a ne'er-do-well in your downtime is all well and good, but should it really be your be-all and end-all?
Im not sure what go big or go home means in this case. Care to elaborate??
But I understand I would need a good motivation. I think that being a skilled thief ties in really well with adventuring as I will be able to disarm traps and pick locks like nobodies business, but do I really Need to stealth around if Im going to act as support for my group during combat/dungeon crawls? Maybe not. For me the fun of DnD isnt powergaming a Combat round successfully. While getting nice rolls IS fun, I get alot out of the game during those moments when I can RP Too. Im not really Into the way a Rogue handles Combat anyways, and prefer a character that stands back and supports. Im sure there are direct ways to move the plot forward through the usefull thief skills aswell.
My Motivation is that While everyone else does next to nothing in town,or inbetween encounters I would like to cause a little drama and maybe get rich doing it. I dont mean to make everyone wait while I go RP a large scale break and enter operation or anything like that. I might try to elicit a quest of that nature that can include the whole party from the DM, by perhaps showcasing my skills as a thief over a few sessions. I think alot of this thought comes from the fact that most of my DMs have left the party Item Hungry, not giving out many opportunities to find some magic Items and such. Same with the Canned Adventures, I feel like all adventures should start with a quest that gets the crew some cool gear. IMHO.
My Point is that Im really only playing around with some skills, and I dont see that affecting my ability to adventure around, much. Maybe you can give me an example of how I might do better
Thief skills like this aren't just downtime activities, though. I think the argument he's making is you're thinking small - while picking pockets and fleecing travelling merchants can sustain you during adventures and possibly turn a tidy profit, these very skills also lend themselves to adventures. They're just not called dungeon crawls - they're called heists or capers if the team likes action, or cons if the team likes intrigue. While the former obviously rewards Sleight of Hand / tools and the latter rewards Decepton, they can call upon each other rather well (there's a reason thieves work in groups - a grifter can manipulate a mark or guard captain to create openings for a thief to work their magic. It's especially deadly if you round out your skillset, but don't forget your crew). You're not breaking into crypts, murdering goblins, and pocketing lost treasure - you're sneaking into corrupt nobles' vaults or royal society balls, manipulating people into giving you an opening, and then running away with their magical heirloom, super-valuable golden idols, and setting them up to get arrested instead of you on your way out.
Being a thief doesn't mean lacking ambition. At higher levels, you might be bored with travellers' purses, and you've got your sights set on the crown jewels. (Although, since "Thieves steal the crown jewels" is a traditional adventure hook (seriously, open any DMG that mentions such hooks, and it'll be there), you might run into another thief crew trying the exact same thing at the same time, which can lead to interesting complications, especially if both your operations depend on not raising the alarm. Or, alternatively, you break into the vault and find the crown already missing - just as the patrols turn up. Now you've got an escape, a whodunnit, and a master thief (in this case, stealing from other thieves, whoever they may be) adventure all in one.)
This isn't intended to be an entire campaign thing, though it easily could be. But if the last three adventures have been you helping the paladin on his holy quest and you've finally vanquished the Evil Lord or something, and before that you were paid to help the wizard on his investigation of ancient ruins, and so on, you've got good reason to say "Hey, guys, can I pick the job this time?" Just make sure the mark is one you can all agree on.
(EDIT: I should mention that Stealth doesn't necessarly refer to hiding behind things. It's avoiding attention in general. Blending in with a crowd, not drawing prying eyes while you're at a noble's soiree when you shouldn't be (especially if, let's say, your archrival from the police is in attendance), slipping away from a social situation when you see your chance to empty the safe, and - if you mess up - giving guards the slip during a chase sequence (which the DMG actually codifies) are all Stealth, though some of them can also be accomplished or aided by Deception (i.e. passing yourself off in disguise to the doorman or maintaining a cover story while inside would be Deception, but avoiding attention altogether rather than misleading suspicion? That's Stealth. It might not necessarly be a Dexterity (Stealth) check so much as a Charisma (Stealth) check, though.)
A thief game doesn't mean everyone's a bard or rogue, though. Consider the general roles involved in a caper crew, and how your team's skills can fill those niches. The paladin plays a sociable honest-man whose credibility gets the team into places (naturally, you finesse the situation so heat's never pinned on him, letting him still do this), and he helps in picking your marks to fulfil his divine oath (maybe your targets are agents of an evil king's inner circle, and he's sworn to overthrow him), and if all else fails he's your muscle, making sure to cover your escape. The fighter is so skilled at fighting that he's capable of overcoming any guards who come your way if the alarm's raised, and his muscle-bound form fits a stolen military uniform much better than your lithe frame, should you need to have someone impersonate a thug or policeman. (What? Fighters can have the Charlatan or Criminal background too!) The wizard is your fantasy tech guy, preparing support spells where you'd expect spies to use unusual gadgets (ranging from Levitate and Spider Climb to Scrying and Dominate Person); his clumsiness in thief situations doesn't matter if he's the getaway car (Teleport). And so on. Just as you license your thief skills at sensing danger and overcoming obstacles undetected to your team when they dive into a delve, you can ask them for their skills when you want to pull off a really amazing heist. (Go ahead and watch a few heist movies and see how they work in diverse skills, especially if there's a crew with a distribution similar to your party!)
That said, you'll definitely need to recalibrate your expectations on magic gear in 5e. It's not common, but at the same time, it's not really needed. Don't expect a lot of magical bling, and expect what you do find to be really special, even if the numbers aren't terribly super-crazy-amazing.
Definitely talk to your DM about what you have in mind and how they would handle the situations. The more info you have, the better equipped you'll be to to build the character you want.
Tempest makes a lot of great points, but that's assuming that style of campaign is what your DM is going for.
Basically, communication is key. Be clear on what your illicit activities entail. "I'm gonna go out and steal as much as I can." isn't going to cut it.
It seems to me that you want to be a master burglar. Disarm any trap, pick any lock, and score the big magical haul. So the keys to a build like this would be a high Dexterity for Stealth and disarming traps/picking locks and a high Wisdom for Perception. Third would be a decent Intelligence for Investigation and Arcana. You'll also need a passable Stength for Atheletics checks.
If you want to be a con man more than a cat burglar, Rogue may not be the best choice. Look into:
Warlock - You can get an invocation that let's you disguise self at will. Another invocation lets you add deception and persuasion as additional skills. You can get invisibility as a spell. You get access to some good illusion spells which open another avenue to deceive and swindle. IMO a Fey Bladelock multiclasses great with a Rogue, though it takes much more character planning(if you go this route, I'd start rogue for three levels to become an arcane trickster, then go warlock for a bit... makes for a very versatile character).
Trickster Domain Cleric - more than anything, this seems like a good choice for you. Clerics have fantastic support spells (you said you prefer a supporting role in combat) and this particular domain covers all your thieving needs - charm person can help you sweet talk anyone, disguise self can get you access to places or let you frame people, pass without trace provides a massive bonus to stealth for your entire party, dimension door gets you to physically hard to reach places, polymorph can let you become a tiny creature and sneak into most areas. Your channel divinity provides you with an illusory copy of yourself and the ability to turn invisible for short periods of time (sounds great for letting a guard pass by). Enhance ability and guidance can help to cover any holes in your skills like lockpicking. Clairvoyance gives you a lookout or security camera. Find traps can help keep you safe.
Aside from thieving, blink and mirror image are fantastic defensive spells. Dominate Person is a powerful spell in various situations. Modify Memory seems extremely useful for intrigue. This class can be done with very limited investment in multiple stats - boost wisdom and dex/charisma with the leftovers (consider the actor feat if you like disguise self). Just be sure to pick a background that gives thieves tools and probably pick sleight of hand for a proficiency because it is harder to buff that than stealth.
Druid 2 can be tasty. Turn into an animal. Sure it's not combat capable, but who notices the CR0 creatures?
A lot of this seems very...personal.
What, exactly, are you trying to do? Rob? Cat-burgle? Murder-for-hire? Petty Theft? Art Thief? A fast-talker (persuasion)? A silver-tongue sneak (deception)?
That, compunded with "what kind of campaign is going to be run" are the two biggest questions that need to be answered before we're giving our OWN personal preferences for how we go about the skullduggery we like. (personally, my favorite assassin tactic is to Polymorph myself into a squirell or an adorable puppy. Then, at night...). But! Maybe that's what you want. A smorgasboard of options to pick-and-choose from 
Things like where are you? What's your party like? What's your DM's style?
I think Arcane Trickster and Transmuter together opens up some pretty solid opportunity for shiesty shenanigans.