In vanilla, your character is given a Vault 21 Jumpsuit, 4 Stimpaks, 18 caps, and a number of bobby pins and weapons based on whether you have a few specific skills tagged. But the items Doc Mitchell gives back to you are supposed to reflect what you were carrying on your person when you were ambushed. Where are the couriers old clothes and supplies? Shouldn't the skills your character favours determine the gear they were carrying in a more significant way? This mod does exactly that.

1.3 Update is here! Added a replacement .esp for compatibility with Character Creation Streamlined, for both the Main version and the Picked Clean version, and all options are now bundled in a convenient FOMOD.

- LIST OF CHANGES -

When you wake up, you will be wearing a Patient Gown, as seems appropriate given the context. This will be removed from you when Doc Mitchell gives you your old gear back.

The basic gear you are given has been adjusted to be a bit more realistic:

A Courier with 3 Luck or less will find that their gear was stolen by the Great Khans, and will start with only the Caravaneer Outfit, the Rawhide Cowboy Hat and the Vault 21 Jumpsuit.

Vault 21 Jumpsuit (Equipped) - Unchanged from vanilla
“Mojave Express Delivery Order (6 of 6)” - Unchanged from vanilla
20 Caps - A tiny, insignificant boost from vanilla, just because I like round numbers
2 Stimpaks - Half the number given in vanilla; Stimpaks are a relatively rare and expensive commodity. You get some food items which helps make up for this loss
Caravaneer Outfit - The Courier wears a very similar garment to this in the intro. At 50% condition, because it's probably covered in your blood and dirt from your grave.
Rawhide Cowboy Hat - Same as above
2 Purified Waters - Makes sense that if the Courier was trekking through the desert, they'd be carrying water and food
Trail Mix - Same as above
.357 Magnum Revolver (Unless Guns or Energy Weapons is tagged) - A more simple, rugged choice for a courier who doesn't specialise in firearms but still needs protection. Has less DPS than a 9mm pistol, especially with .38 Special
30 .38 Special Rounds (Unless Guns or Energy Weapons is tagged) - Cheap ammo that has less kick than magnum rounds, for couriers who aren't used to shooting guns. Can't be sold for some easy caps, and lowers the DPS of the revolver you're given. If you want a better pistol, pick Guns as a tag skill.

Before, only 6 skills influenced your starting gear when they were tagged, and Melee and Unarmed gave you some really underwhelming options. Now, all skills will give you a few extra items:

Barter - 80 caps - An extra bundle of caps for characters who like to trade
Energy Weapons - Laser Pistol + 30 SEC Bulk (Replaces .357 Magnum Revolver & Ammo) - I made the ammo Bulk to lower it's value, and make sure that it doesn't totally trump any other weapon option
Explosives - 4 Dynamite + 2 Powder Charge - In vanilla, you received 8 Dynamite, which I thought was a little too much. Threw some early-game mines in there too for good measure
Guns - 9mm Pistol + 39 9mm Rounds (Replaces .357 Magnum Revolver & Ammo) - A higher-DPS, semi-auto pistol to replace the revolver
Lockpick - 10 Bobby Pins + 30 Caps - You now only get bobby pins if you have Lockpick tagged, as opposed to vanilla. Also gives you a handful of extra caps, to represent spoils gained from locked containers
Medicine - RadAway + Doctors Bag - Some essential medical supplies that should help in the early game, without going overboard
Melee Weapons - Machete - The straight razor in vanilla was pathetic, why would someone choose it over a more practical weapon? The machete makes much more sense, as an effective self defence weapon and as a multi-tool for long journeys. Couriers who use melee in the early game are at a disadvantage, so a decent weapon should help ameliorate that.
Repair - All weapons are at 85% condition rather than 50% - A simple, useful bonus that reflects couriers who are good at maintaining their equipment
Science - Atomic Cocktail + Rad-X + Mentats - A bundle of chems that should help the early game. I deliberately chose chems that were less incriminating or "seedy" than other options, like jet or psycho
Sneak - Cateye + 4 Throwing Knives - Silent and concealable ranged weapons (plus, throwing knives are weirdly hard to come by in vanilla) and an aid for night-time clandestine activities. The alternative was to give the player a stealth boy, which I felt might have been a touch overboard
Speech - Meeting People magazine + 2 random magazines + Whiskey  - A few magazines to help with skill checks or combat, and a wee dram of whiskey for when you need to get your charm on
Survival - Binoculars + 2 Antivenom + Gecko Steak - Just some basic survival gear, plus antivenoms aren't too common in the early game and are VERY helpful if you bump into some radscorpions. Also a little extra food, as the survival-orientated courier would have probably done a little hunting
Unarmed - Brass Knuckles - Boxing gloves were a bit of a bizarre choice for vanilla, they're not that easy to carry around and are specifically designed for sporting use, rather than self-defence, so I gave the player brass knuckles instead, which deal plenty of raw damage and are still an easy to carry self-defence weapon. Couriers who use unarmed in the early game are at a disadvantage, so a decent weapon should help ameliorate that.

On top of all that, if you chose the Four Eyes trait, you will be given a pair of Reading Glasses, because the vanilla game apparently hates you and decided to leave you blind.

Overall, the changes above are designed to only impact the first few hours of play; within that time, you'll probably find better equipment, or more AID items and caps. These changes were intended to be small, realistic and immersive, rather than grant the courier eternal boons based on their starting stats. Technically, if you didn't tag a weapons skills, you might be slightly worse off than in vanilla, but RPGs are about choices and consequences, and the consequences of not specialising in any form of damage-dealing skills is not being able to deal as much damage from the start. Who would've thunk?

Optional File: Picked Clean - The Great Khans looted all your valuables after you were left for dead, so all you'll start with is clothing, and the Vault 21 Jumpsuit that Doc Mitchell gives you, regardless of your Luck stat. Suited for players who want a little extra challenge.

Recommended for use with Jsawyer Ultimate, because having the Courier's Stash items at the beginning is pretty ridiculous and makes this mod entirely worthless.

Also, check out Viva New Vegas, its pretty much the best mod guide available.