Huh, missed that one the first time around.
I don't normally meta-CYOA but for a world as utterly cursed as ASoIaF, and a CYOA as ungenerous as this one, Imma pull out the
Cheater's Chest.
Because I like rolling for random effects, my go-to is normally Dice of Fate but this CYOA utterly fails at giving me any dice rolls so I'll pass. Because it spells out the numbers, the magic pencil would let me edit "you get three blessings" into "you get thirteen blessings" within it's three letter limit.
However this being ASoIaF, Imma go with the Chains of Olympus. I get six blessings (suck it you seven), I'm physically twice as strong as a human of my build should be, any spells I cast have twice the power and duration for a person of my training, and all other benefits I'd get free are doubled.
@BlackDragon98 took the build I'd normally go for already (who doesn't want a dragon? Also the free cities are way better.) So I'm taking Dorne, which tends to be well-protected by it's various natural defenses and doesn't get hit much in the books. The fact that it's much warmer won't hurt when Winter comes. Staying male because @^%$ being female in a world where rape is that common.
I get two jobs free so I'll go with Blade and Coin. Buying and selling will be my primary occupation and the Blade will come into play when I meet bandits or snooty nobles who mistakenly believe they're entitled to a 100% discount on my wares. I'll expend two blessings to get Higher Education on both.
I get two gifts free and those will be Tools of the Trade for a Valyrian steel blade and Giant's Blood to be even more ridiculously strong. I'll expend three blessings to get Valar Morghulis, Touched by Magic, and Grace and Beauty.
Disadvantages: $%^& no, none of those!
The rest will go towards getting a nice mix of companions and setting up my party. I get two free companions and they will be Muwari Vaballatha and Jon Sharp. Rather than a sugar daddy Muwari will be my adviser in the trade. John Sharp will follow anybody honorable and the most honorable person in Westeros is basically average Joe by our standards so I should have no problem being the most honorable guy he's ever seen. For two additional blessings I'll take Corton Penrose to be my magical teacher and Tarrina Gargalen fits this character since I'm also from Dorne and might know her.
We'll be the officers of a merchant company and charter a ship, hauling goods between Dorne and Qarth (unless Muwari's issues prevent him from ever returning to Qarth in which case adjust our typical routes a bit) with stops in Essos and possibly even sometimes trading stuff with the Dothraki . It's not like they can possibly be operating any mines with their lifestyle so they must be getting iron for their swords from somewhere. Granted there's the question of what the heck they're selling me since they apparently have nothing but grass and horses (I mean honestly their lifestyle shouldn't be possible anyway but whatevs). I can probably get their respect via fighting prowess, with Chains of Olympus I'm twice as strong as a I should be and with higher education on The Blade I should count as at least moderately physically conditioned. Were I an average male of about 200 pounds that should put my Bench Press at around 500 pounds, for comparison Dwayne "The Rock" Johnson is about 450. But I'm not average sized, I'm giant blooded, so quite likely I'm more around 1,000 pound bench press. Coupled with being a master water dancer with a a Valyrian Steel sword, I suspect I won't have a problem wowing them and convincing them I'm worthy to trade with.
Depending on the timeline, see if I can recruit Viserys and Daenerys during the period of time they were street urchins and starving before Illyrio got them. That would be significantly better for them (they won't starve as much) and me (they'll be much more appreciate and amenable) and get a superior outcome, before Illyrio poisoned Visery's mind with dreams of conquest. Potentially get them to abandon the idea of rulership and instead embrace the seafaring merchant lifestyle. With the canon truly off the rails we may never find those dragon eggs but then again we're wealthy travelling merchants with significant magical power behind us, we may find them anyway. Alternately just try to get them to embrace a saner outlook on life before getting together with Varys.
Probably have to use Valar Morghulis to kill Cersei. By itself that will probably save Westeros from a lot of it's ridiculous wars. If necessary, burn the second use on Baelish though he seems more vulnerable to regular assassination and I'll try that first. The last one try to spend on the Night King though I suspect he's beyond the abilities of a Faceless Man. Alternately if Illyrio already has Viserys and Daenerys I may have to burn a use on him to get them on board.
When visiting Dorne the Targaeryns will learn the joys of
Black Walnut Hull.