Here is my conversion of Icar from A2. I think he would be a good challenge for your Rogue friend. Note: Icar is blind.
Icar Level 7 Fighter
CR 7, HD 7d10+14, HP 60; Init +3; Spd 20 ft, AC 17 (+7 Half Plate);
Atks +12/+10 melee (2d6+7, 19-20, +1 Greatsword),
SV Fort +7, Ref +5, Will +8; Str 17, Dex 16, Con 15, Int 12, Wis 19, Cha 14;
skills: Listen +19, Intuit Direction +9, Intimidate +7, Climb +9 (-7 check penalty), Craft (Wood Carving) +2, Jump +4 (-7 check penalty), Swim +4, Diplomacy +2.5
Feats: Blind-Fight, Skill Knack(Listen), Cosmopolitan (Listen), Dodge, Iron Will, Weapon Focus(Greatsword), Blindsight 5-foot radius, Weapon Specialization (Greatsword)
Languages: Common, Goblin
Note: he has a Ring of Elemental Fire Resistance Major, Cosmpolitan can be found in the Forgotten Realms Campaign Setting and Blinsight 5-foot radius can be found in Sword and Fist, see end of document for details on Skill Knack
SKILL KNACK [General, Trait]
COPYRIGHT 2001, Carl Cramér
You have some special quality that enhances one of your skills
Benefit: Choose a skill, such as ride. You have a special knack with that skill. You must have some special ability, such as long limbs for climbers; long fingers for pick pockets, lightning calculator for profession (bookkeeper) or being double-jointed for escape artist. You get a +3 bonus with the skill in question.
Special: You can gain this feat multiple times. Its effects do not stack. Each time you take the feat, it applies to a different skill. The bonus does stack with the bonuses provided by skill learning feats, so you can take several feats to be ultra-specialized in a skill. Anyone can use a sense motive check to get a hunch about you (PHB). If the result is at least a 10, they are able to tell which skill you have a Skill Knack for from your appearance.
Notes: Because you must be somehow extra qualified for the skill in question, your character description should make allowance for such an aptitude. This means you can only pick Skill Knack when creating your character or be the result of some extraordinary event in the characters career, such as being 'gifted' with donkey ears from a curse for a Skill Knack to the listen skill or getting bowlegged from countless hours in the saddle.
Balance: 3.88 (Purp 3.50, Pow 4.30, Port 4.00, Comp 4.00, Rule 3.60)
Comments: Remember, it can only be taken at 1st level (as a standard trait), or when something happens to the character that would accentuate the skill chosen.