So I'm stepping back into Skyrim tonight after being away for far too long, my one and only previous play through as a bristling Nord (200+hours) was fun but this time I'm going to be bypassing the main storyline, I'll also only be partaking in the thieves guild side quests (for obvious reasons).

A few questions:

1. What race is best for a thief character?
2. Is there anything of real value for a thief to pilfer in Skyrim?
3. Are there any fences? (don't remember meeting any in my previous playthrough)
4. What would be the best perk set's to choose for a thief?
5. What would be the best type of clothing?
6. Is there a Skeleton Key?

Kind regards

1. Breton. Bretons are best at everything.

2. There are places worth pilfering. Any building marked with the "loot" shadowmark is worth hitting.

3. Yes; you unlock them by doing Thieves' Guild quests.

4. Strangely, heavily perking the Lockpicking and Pickpocket skills makes thieving stupidly easy, as does putting more than one or two points into the Stealth perk of the Sneak tree. At least that's been my experience. So it's up to you and what kind of thief you want, really - though I wouldn't neglect combat skills.

5. I go with light armor, though I've been tempted to use just regular street clothes.

6. Yes, unlockable through a Thieves' Guild quest.

Any race would be good.

Jewels and small household items are valuable when sold at large quantities to fences.

Only in the thieves guild, but if you're on PC there are mods to add shady vendors.

Perk set is really just your preference as a thief.

Hooded light armour for combat, keep some clothes in public.

The only thing I can add is that Khajiit's and Wood Elves are traditionally the best thieves. Argonians and Redguards also fit the bill. Mainly because the Hammerfell clothes look sixy as hell!

I'd impose some limitations on carry weight and money

Restrict yourself to a base carry weight of 80 plus your level. For example, if you're at level 18, then your base carry weight would be 98.

Then subtract for gold, where every 100 gold reduces carry weight by 1. For example, if your base carry weight is 98, and you have 457 gold, then you subtract 4. Your effective carry weight is then 94. (Notice that you can always carry up to 99 gold without penalty).

This might seem complicated, but it's not as hard as it seems. You can easily write the formula into a spreadsheet to use as a calculator or produce a reference table.

Now why on earth would you want to go to all this trouble? The reasons are two-fold.

First, by gimping your carry weight, if forces you to be more selective about what you steal. You can't just break into a house and walk off with everything but the kitchen sink stuffed into your back pocket. It also helps to keep you in character, so to speak.

Second, it creates a trade-off between holding money and other valuable items. Normally, more money is always better, and you convert all non-useful valuables into money at the first opportunity, because money is weightless and can carried in unlimited quantities and is highly liquid, i.e. you can spend it anywhere. However, with the trade-off, it can sometimes be advantageous to hold onto valuable items which weigh less than the corresponding amount of gold. It also forces you to store your excess gold somewhere rather than carry your entire fortune in your little purse all the time.

In other words, these rules might get you to think more like a thief.

EDIT: Where 'B1' is your level and 'B2' is your gold, then this formula calculates your carry weight in a spreadsheet. I'd bump the base carry weight from 80 to 100 if you want to use heavy armor.

=ROUNDUP(80+B1-B2/100)