I am a master thief. Let’s do some spoiler-free tips.

Yes you can earn a lot of gold. When I was pushing for my million gold fenced achievement I was pulling in $40k/day through fencing, plus maybe another $20-$30 in various quest rewards and bonuses like motifs.

Why are Khajiit strongest for thieving? They get a racial passive to decrease their detect radius AND a 5% pickpocketing buff. Wood elves are a close second, with just the detect radius. Orc sprint doesn’t come into play...you’re not really going to struggle escaping when you need to.

Why are nightblades strongest? Cloak. Being able to cloak past guards when you have a bounty is way helpful. When you pickpocket you can use cloak to “reset” your hiding. Magblades get a bit of speed if they slot concealed weapon. But I’d prefer a stamina Khajiit over a magblade, honestly. And if this is a thieving character I’d just morph for the concealed weapon on my Khajiit anyway and use it as a speed buff. (The downside is that it won’t deal much damage, but on a thieving character I can get away without it as a damage skill).

Medium armor, assuming a stamina character. You want stamina, sneak cost reduction and dodge roll. You won’t need tankiness from heavy or the magic from light.

Weapon: the only thing to mention for thieving is bow offers a short speed boost when you roll. I usually dw/bow when I set up for stealing. I put cloak on my bow bar.

Helpful skills: retreating maneuver for speed, vigor or other heal in case you need it, cloak, concealed weapon for speed. You shouldn’t be under threat a lot, but if you tend to get guards on you bow’s draining shot will push them away, stun them and heal you.

Helpful sets: night silence for stam and shadow dancer for magic. These eliminate the sneak speed penalty. Another reason I prefer stam...a player can become a 2 crate crafter in a few days and make their own desired piece/trait night silence. Another set is Night Terror. On the third piece you get sneak cost reduction and stealth detect reduction. Night mothers embrace is another sneak and detect reduce set. (NOT the craft set, which is Night Mother’s GAZE. This is a drop set).

Vampire: also eliminates sneak speed penalty, opening up slots for a different set. A vamp Khajiit in NM embrace and night terror might be the sneakiest possible setup.

Jewelry: Summerset will allows speed traits on jewelry. Speedy thieving gear will be nice.

Legerdemain: the higher you’re level, the better your looting. But you want to speed level this to level 16 to get passives for 40% sneak cost reduction. You want this on a stam or magic character. (Even non-thieves...it’s very powerful). To speed level legerdemain, go to the ships in Daggerfall. There are very few npcs. Steal everything. Don’t forget below deck! Fence it all for your daily max. In a week or so you’ll be leger 16. On a thief character, you can invest in the first three leger passives. You won’t need lockpicking or the bounty one.

Thieves guild line: these are mostly good passives and are each self explanatory.

Boost your thieving income w repeatables: in the thieves guild den in hews there is a npc named Karri w a board that offers unlimited respawning thieving quests. You will be asked to pickpocket in three specific zones, loot safes in three specific zones, or find a specific stolen item for a countess. If you’re going to pickpocket for income, you might as well do this while running these quests. You’ll get some valuable rewards, maybe most notable a lot of $500 bounty reduction certificates. These certificates will keep you in the thieving business without a lot of pausing for the bounties to run out. (Note...you might want to occasionally rack up and pay a bounty if you want the achievement for paying $100k in bounties, or the one for escaping guards)

Or boost income with dailies: once you are level 2+ in thieves guild and dark brotherhood, you can do dailies in their respective dens. These are made for speed thief nightblades. They will yield a lot of stolen loot, they’ll advance the skill lines, and when you get to a point where you can perform them flawless you will get a motif half the time...these are worth about $15,000 gold per page.

Pickpocket vvardenfell. Dark elves are ***. Lol. Picking the small towns in this zone offers a shot at the three house motifs. These are worth $10-$20k per page. It’s on an rpg with a timer. Usually I get one within 100 pickpockets (at three per npc). Then once a motif drops you’re locked out for 4-5 hours.

Happy thieving!