So, ummm...
Lots of Dex, quite a bit of Str, 14 Wis, maybe 12 Int (skillz).
Rogue 1: Combat Reflexes. Lots of skills. Max Tumble, Bluff, skill monkey.
You can hit stuff that tries to go around you. You can try and go around them as well. But you can stab them in the back of the head.
Fighter 1: Bonus Feat - Exotic Weapon Proficiency (Chain). Whatever skill.
You found some chain with some lead on the end. You have found your calling in life. It is to hit things with this chain, in the most painful yet safe-to-yourself way possible. You've probably also got a shortbow, but that's just a tool. The chain is where it's at
Rogue 2: TWF feat! More Tumble/Bluff and other stuff.
1d6 SA with easy flanking, but also hit-moving-things response to DM's actions. Or hit stuff twice. You choose.
Rogue 3: Keep up tumble and bluff. Max other skills or point around stuff.
2d6 reached melee SA, which is great. Gets even better next level (big better). +Dex attribute gain, or whatever a 44pt buy just managed to miss out on. How?
Psychic Warrior 1: Up the Walls feat. Expansion power.
Awesome rogue at the beginning of every encounter, and awesome fighter with tons of options once a day for a minute, but no more wall walkies afterwards until you've had a nap. Big red button, but no easy flank afterwards. 20' range with a combat reflexes, trip'y, disarm'y Chain is good when you're big. Walk up walls is better.
Rogue 4->Lots of levels: Skill stuff, whatever. Psionic Talent feat at character level 6 (now). Penetrating strike at 10th (SRD or CC p51). Pretty simple feat.
Now the big berserk button is press-able a couple of times a day, and you can still wall walk after it. Buy cognizance crystals for more beserk button. Stay focused. Maybe introduce him to the concept of Shards as an item, just so he can do other rogue stuff well, but at a price.
Pretty easy, pretty cool, easy-mode rogue. Do stuff when rogue, go sick when big. Done! 6 levels of awesome, 1 feat/power/weapon/class level that's not PHB/SRD original. Easy to learn, easy to learn other stuff later, fairly boots backside in everything rogue'ish.
Edit: Duh. Rogue skills first x 4. Gives a more methodical progression to the awesome anyway, but with more skillz.