No matter what type of thief you wish to play, you will need Stealing. The higher your stealing, the heavier items become easier to steal. You get noticed less stealing as well – so it’s wise to plan on getting 100 Stealing for whatever your play style.
There are two methods of stealing: Random and Target stealing. Target stealing is the activity of opening a person’s paper doll, opening their backpacks, and place the stealing cursor on the item you want. Random stealing is simply placing the stealing cursor on the person’s body, and the computer does a ‘blind’ grab into the pack and goes after ANY item it chooses. There is a chance it will target items too heavy or those that are not stealable.
The general rule of thumb is that you can steal items that are one-tenth in stone weight your stealing skill (ie, with 50 skill, you can only steal up to 5 stone items). At levels of 70 though, you will notice that sometimes you can steal 10 stone items, random or targeted. To gain skill in stealing, always try and steal a little more than one-tenth your skill.
It's harder to target steal than random. Steal items with 1/10th your skill level and a little less so you can gain on your successful thefts. At medium to higher levels, you may notice that you can successfully steal items over 75% of the time. I suggest you raise that item one stone in weight to make it 50% success.
You need to cycle your items at all times, and have a large number of items. OSI instituted a anti-macro code, which means you can only gain so much off a single item, then you must move onto another. I find that 100 Items is best for this, whether it be 100 dye tubs, 100 kindling, whatever. Just steal each item in a row then start over. At 85+ skill, 100 items seems to be too little, so every day start with entirely new items.
So what is a young thief to do?
If you just started, you should have 0-50 skill. Easy thing to do is escorting nobles and seekers of adventure outside of guard zones and robbing them. Good towns for this are Skara Brae, Moonglow, Magencia, and Jhelom. Snoop them first and pick one with enough gold to cover your stealing skill. If you are in Power Hour, target steal their gold. If you are not in Power hour, simply random steal from the noble. You’ll go gray from this easily and will be freely attackable. This method only works in Feluca.
A safer but more expensive method to gain is to buy a packhorse and fill his pack with Crystall balls, Dye Tubs (10 stone items) and large amounts of stacked items like bandages (get them from wandering healers in the woods), kindling and empty bottles. Take your horse to a very busy area (banks in major towns are best). Now it is important to say, ‘All Guard Me’ to your horse, this way you can steal from him and NOT turn gray (turning gray in town will quickly get the guards after you). Once the packhorse is guarding you, steal away. use items you can successfully steal. The packhorse method only works in Feluca.
For those that do not wish to Travel Feluca for gaining stealing, you are cheating yourself out of the easiest ways to gain. However, it’s possible to gain stealing in Trammel. My personal favorite method was the Bone Knight Room in Deceit. But pick anywhere that is crowded where folks like to practice, Jhelom Pits for example. While here, you can gain in a variety of skills : Fighting, Anatomy, Healing, Parry, Arms Lore, Item ID, and even stealing. Simply place a bag on the ground, and put items into the bag, then steal from it. There are normally enough people here to observe you robbing the bag on the ground and you can gain. You do turn gray here as well – if you die down here, you become freely lootable even before your body turns to bones. This works great till you hit the 70-80’s, then it just isn’t as good as the packhorse method. This works great though for young thieves that need to hone other skills while down here, Wooden Shields weigh 5 stones, put a bag in a bag for 6 stones. Add a gem, bottle of ale, bandage, or any 1 stone item you find on the Bone knight Corpses to add 1 stone to the bags as you go.
Some further advice is to use UO Assist while training. Put 66 dye tubs/crystall balls on your packhorse. Then record a macro for stealing each and every tub. A delay of 10,000 or more between steals must be inserted in the UO Assist Macro menu. After the last tub, insert a action or event to notify you that the macro is finished and you can start it again (Play an instrument, Speak, open your backpack, cast a simple spell, etc etc). I say 66 tubs because UOAssist has a limit on how large a macro can be – and that’s the limit.