A nonpsionic Thri-Kreen (only +1 LA instead of +2, found in MM2 and Shining South) Racial HD 2/ Monk 1/ Soulknife 2/ Soulbow 2 would be a superb choice. Get Zen Archery so Wis is your only important ability score for attack/damage/AC. Take Multiweapon Fighting (MM) and fire four Mind Arrows/round, each of which could have the Lucky property so every missed attack would have a second chance to hit. Your Weapon Focus: Mind Blade bonus feat from Soulknife will apply to Mind Arrows as well, and if you can use the variant Monk fighting styles from UA the Sleeping Tiger style would grant Weapon Finesse just in case you get into melee. With a flaw you could have enough general feats to get Vow of Poverty, which is just amazing for what’s already one of the strongest archery builds around, in which case I’d go with Noncombatant.
Since you know you’re going up against a dragon, you should probably try to make sure everyone has Evasion and good saves across the board. The Draconomicon has more than enough resources to make these critters unstoppable. With their racial Frightful Presence or the feat Awaken Frightful Presence if they’re not old enough to have it, plus a feat called Frightful Presence, and you’ll have a Shaken x2 = Frightened party from the start of combat who will all have to reattempt the saves throughout the battle until they’ve succeeded on each one. The Metabreath feats, particularly Maximize Breath and Clinging Breath, will allow it to use hit-and-run tactics to deal extraordinary amounts of damage if it makes the breath attack cling for multiple rounds. Keep in mind that the party may be fighting on a cloudy day, in fog, or even during a blinding snowstorm which has little effect on a dragon’s ability to fly but would toss smaller PCs through the air if they try to take flight. In that case, you should definitely look at some of the spells in Frostburn, particularly Snowsight (druid/ranger/winter domain 1, 1 hr/level, 50g each for potions, everyone get at least 2 in case it uses dispel).
Another option would be to stick with a winged Dragonborn but maybe not Water Orc, and go Fighter 2/ Paladin 6. Take Exotic Weapon Proficiency: Ritiik (Frostburn), Power Attack, Combat Expertise, Improved Trip, Extra Smiting (CW), and use the Charging Smite variant from PHB2. For a Dragonborn Water Orc your ability scores would probably go Str 20, Dex 10, Con 14, Int 13, Wis 12, Cha 12 after racial adjustments and both level-up points in Str. Get a +1 Valorous (UE) Ritiik (FB), or if you can’t get Valorous then probably get Lucky (XPH). Other gear will be Gloves of Str +2, Cloak of Cha +2, Vest of Resistance +2, +1 Chain Shirt, Ring of Protection +1, three 1st level Pearls of Power, and 300 gold to spend on potions, scrolls, wands (with only a few charges), tanglefoot bags, nets, etc.
You’ll probably need other party members to use nets or tanglefoot bags to keep it from flying too far away so you can spend one round flying up and another to use a Dive Attack. Power Attack two-handed for -3 to hit, combined with +8 bab, +6 str, +2 charging, +2 smite evil, and a +1 weapon will give you +16 to hit. Your 1st level spell prepared will be Rhino’s Rush (SC), which is cast as a Swift Action just before the charge. Assuming you hit, you’ll deal 1d8+1 weapon, +9 str, +6 smite evil, +12 charging smite, +6 power attack, x2 for Dive Attack, x2 for Rhino’s Rush, and x2 for Valorous for a total of x4 damage which is 4d8+136 damage. Your opponent must then make a Reflex save (DC 10 + damage dealt!) or be hooked by the Ritiik. Once hooked you get to make a free trip attempt, at a +10 bonus, which if successful gives you a free additional attack due to Improved Trip, which still has Power Attack and Charging applied but none of the smite or multiplier bonuses. Once all that is over with you can rip the Ritiik free, dealing just as much damage as the initial attack (whatever the result of the 4d8+136 was). If you fail to kill it in one attack, you simply retreat and use a Pearl of Power to recover Rhino’s Rush, then repeat the process. Don’t forget that it must save vs massive damage for both the initial attack and when ripping the weapon free.
At that level Enervation is available and is definitely a viable choice due to the low touch AC of most dragons. A Spellscale (RotD) or Human with Draconic Heritage Sorcerer with Split Ray (CA), Practical Metamagic (RotD), and Arcane Thesis (PH2) can cast a Split Ray Enervation without having to use a higher level spell slot than normal. The Metamagic Specialist variant (PH2) can be used to overcome the increased casting time several times per day. This trick is made difficult by the prerequisites of Practical Metamagic and Arcane Thesis, as neither can be taken any sooner than 6th level. Additionally, you must already be able to cast Enervation to choose it as your Arcane Thesis, but where there is a will there is a way. Upon reaching 8th level, the character could have spent years studying Enervation and learning all there was to know about it, sacrificing his physical health in the process gaining the Feeble or Frail flaw, or becoming severely near-sighted from pouring over tomes for so long gaining the Murky-Eyed flaw, or habitually becoming too focused on the task at hand gaining the Inattentive flaw, in order to develop his Arcane Thesis on Enervation at 8th level. This would enable you to cast a Split Ray Enervation every round until you run out of 4th level spells (at least 3), dealing 2d4 negative levels per round assuming both rays hit. This sort of character would be the proverbial “glass cannon” capable of dishing out massive offensive power but easily defeated by a strong counteroffensive, though your 1st through 3rd level spells will likely help out with that. The Stalwart Sorcerer variant (CM) would probably be a decent choice just for the HP bonus.
Another nasty trick would be for someone to get a Scroll of Prismatic Wall (hopefully a character who’s built to not fail at the caster level check). Ready an action for when the dragon is flying and in range. Cast the Prismatic Wall directly in front of it, and if its maneuverability is Average or worse it has no choice but to fly through the wall suffering the effects of every color. Logically this will work infallibly, but as-written it could choose to drop straight down instead of flying into the wall, though I’d at least have it make a Reflex save (at the spell’s DC) to react quickly enough to avoid it. This is entirely dependent on it both having less than Good maneuverability and lacking the feat Hover, and even then it may not be a guaranteed victory, so it may not be worth the high cost and risk of using such a high level scroll.
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