Hey shadowbloodmoon...
It's getting there... it's certainly getting there. I really like many of the aspects you are beginning to play up.. and as you do, I'm finding some of your other choices are slowly falling by the wayside and which we can change in order to create a cohesive whole. Having read the whole thing now edited... I'm thinking that it could do with a "re-write" as it were, rather than a simple edit. This way you can recreate the story as a cohesive whole, rather than leaving it a bit disjointed where you added/sbtracted certain areas in certain drafts. Plus, there's some timeline problems I found in there, which I'm sure you'll want to fix up. So let's go through the current incarnation step-by-step, shall we?
I think the new intro to Jason really works. Having Mark (presumably an older brother) following his father around and learning the family business, while Jason remained at home twiddling his thumbs is a cool concept and it really sets the groundwork for the character. I'm wondering whether you want to leave it 14 years old that he leaves (with the hired guns following him) because of what you have happening to him later on... but we can figure that out as we go along (another option might be him just running away at like 16 or so with no one following him).
Then he goes on his travels. Here is where I think you need to go some reconfiguing of your story, because you tried to squeeze both my suggestions into the same character... world traveller PLUS eight years in a Buddhist monestary. It really needs to be one or the other, because your timeline had him leaving home at 14, he spent 8 years in a monestary learning Buddhist ways, he then spent 12 more years spanning the globe before returning home two decades after leaving, then he spent countless years working criminal activities before taking down his family's syndicate then somehow getting into the CIA. This would make the character probably upwards of 40 years old... which is not what I think you were going for, if I'm not mistaken.
The problem I think you've run into is that you're trying to keep your five specialities you selected and jury-rig a history to encompass all of them. And your five specialties are so different from one another, it's not making much character sense to keep them all, and thus is hanstringing your history.
As I've said previously... your characters already know how to do EVERYTHING... and do them all very well. In D&D terms... every one of your characters have max ranks in all the D&D skills. You all are master marksmen, you all can fly jets, you can all sneak through darkened areas, you all have contacts around the world, you all can speak multiple languages, you all can influence people. You have every skill you might need. All the five specialties are, are those five skills in D&D that you not only have max ranks in, but also have the Skill Focus feat in as well. You're just that much better at that one particular thing than the agents around you. But the only way you gain that skill focus is having it be an integrated part of your character's history... something that is very specific and has been an integral part of your character's make-up from the beginning.
So that being said... you need to decide which history you want to go with... world traveller OR Buddhist monk (or some other plot you might come up with). It doesn't matter what. The important thing though is to create a history outside the perview of "what specialties will I gain by doing this path?" The specialties are secondary. They should have no influence on the history you create. So if we go by the way of "Monk", here's what happens...
"Multicultural" is taken out automatically because it's way too vague a specialty. You're already a spy... you've spent years studying all the different cultures as part of your espionage training. Just like every other spy out there. And there's just way too much culture out there world-wide for anyone to be more "multi"cultural than someone else. Now if you wanted to selected a SPECIFIC culture and a specific part of that culture... that's more than cool. Like if you kept your Buddhist monk training part of your history... "Eastern Philosophy" makes terrific sense, and it's a specific specialty that you might have over other spies in the agency.
"Hand-to-hand combat" is fine if you also keep your Buddhist monk part of your history. No problems there. However if you go the route of the "world traveller" history... you wouldn't have spent enough time and enough years working at your hand-to-hand to be any more appreciably skilled than any other agent out there.
"Evasion" doesn't really work for this character as written. Your basis for the skill was avoiding the hired guns that were following you... however, if you stick with the monk history, you said you spent eight years in the monestary, and there's no way in hell the monks would allow two or three guys with guns to hang around watching Jason meditate for years on end. So there's be no reason for him to know how to evade people (moreso than any other regular spy). Even with the world traveller option... at some point having chaperones becomes useless because as you yourself said... his father didn't care about Jason at all, so why waste men to follow his galavanting son across the globe (especially after he reaches the age of 18?) Thus having Evasion as a specific specialty doesn't really work.
"Human Networking"... again, it's too vague a specialty, especially for someone as anti-social as Jason. Why is Jason better at making friends and contacts across the globe than any other agent? Just because he's gone to many different places? Nope... his life would have to have entirely geared towards networking for him to have a specialty above and beyond any regular field agents. A salesman I could possibly see having "Networking" as a speciality... but even then, the people he networked then probably would do him no good in the spy business.
Finally, "Military weapon identification". This I'm sort of okay with... because knowledge skills are a lot easier to justify having because it's simply a matter of studying up on the subject... reading hundreds of books on it and so on. However, I would say that Jason would need to have more interest in that subject and have spent more years learning up on it than just the finally couple of years he spent in the CIA before joining Espion. You don't become an "absolute expert" on anything unless you have an overwhelming interest in the subject above and beyond the normal person studying up on it. I like to think I'm an expert on D&D... but you put me in a room with other roleplayers, there's probably hundreds of people who have more rules completely memorized (with page numbers and everything) than I could possibly have. I would certainly not consider myself to have a speciality in "D&D", even though I've played it for fifteen plus years. And that's the same way you need to think of the knowledge specialties.
So all in all... I think what you should do to help yourself out is create a timeline for yourself as to when and where did each step of Jason's life take him on his journey towards joining the CIA? And you don't need to skimp on his history once he joined the CIA either... his work with them would probably have more of an impact on his career in Espion than anything he learned as a teenager jet-setting from place to place. Once you've got a cohesive history banged out of when he left home... the specific places he went to on his travels... when he returned home... what he did against his brother... how and when he joined the CIA... and what he did in the CIA before moving to Espion... then you'll be able to re-write your history and take out all those extras bits from earlier drafts that don't really have a place in the character as he stands. And don't worry so much about finding places to put specialties inside the history... we'll be able to find them ourselves after the history is completed. Cool? Sweet!
Yes, this is hard damn work and not something any of us could just bang out in twenty minutes... but this is why I said you'd have to get used to me, as I'd get used to all of you. It's working together to create characters of depth that are half the fun of playing the game in the first place.
