I see the 2d20 being a good way of simulating a character who is expert in what the dice roll is representing rather than luck (even though such a luck mechanic has been common enough in D&D).
Could this be the answer to multiple attacks and/or weapon specialization? At 7th level, the fighter rolls 2d20 for all attacks and takes the better. At 14th level, he rolls 3d20 and keeps the best.
I could probably add some structure around that to make it feel more like multiple attacks or super-specialization, too. Maybe grant the bonus rolls for free and then have a feat tree or two to represent different focuses.
Power Attack
Prerequisite: two or more attack rolls.
Effect: Starting with the highest die rolled, compare the result to your target's AC. If only the highest result would hit, do normal damage. If the second highest roll would also hit, add a competence bonus equal to your strength bonus (1.5 str bonus for two-handed weapons) to the damage dealt.
Improved Power Attack
Prerequisite: Power Attack, three or more attack rolls.
Effect: As per Power Attack, plus if you have a third attack roll and it also would hit, the bonus increases to double your strength bonus (triple for two-handed weapons).
Whirlwind Attack
Prerequisite: two or more attack roles.
Effect: If your highest attack roll would hit your target, pick a second target you threaten. If your second highest attack roll would hit that target, that target takes half the damage you role against the primary target.
Improved Whirlwind Attack
Prerequisite: Whirlwind Attack, three or more attack rolls.
Effect: As per Whirlwind Attack, plus if the second attack hits, and you have a third attack roll, you may choose a tertiary opponent you threaten to compare this roll against. If it succeeds, this target also takes half the damage rolled.
Weapon Specialization
Prerequisites: proficiency in weapon, two or more attack roles.
Effect: If only your highest attack would hit your target, apply damage as normal. If your second highest attack would also hit, apply half your BAB (formula assumes 3e BAB) to the damage dealt.
Weapon Mastery
Prerequisites: Weapon Specialization in weapon, three or more attack roles.
Effect: As per Weapon Specialization, but if your second and third attacks also hit, you apply your full BAB to the damage dealt.
I have a couple ideas on Weapon Finesse and Two Weapon Fighting, but you get the point.
Edit: I'd also see the stylistic modes (power, whirlwind, finesse) being mutually exclusive, but specialization (and, maybe TWF) being additive. You could also add other feats allowing combinations, like:
Berserker
Prerequisites: Power Attack, Whirlwind Attack
Effect: The effects of Power Attack and Whirlwind attack are cumulative. Apply Power Attack damage to the first target before calculating damage to the secondary target.