Hi Fenton,
When comparing this version to the previous version the most important thing I saw was a change in Jacob's character. On the website you state that he: A) Is forced into doing/studying what he doesn't want to do/study, and B) He isn't motivated (failed all his exams, and is almost kicked out of school for lack of concentration). So I'd say: he's rebelious towards his parents and teachers, and - probably - all other authority-figures.
Based on this assumption, I'd say the second version is the better of the two. Since the original version had tidy cloths and a neatly cut hairstyle, whereas the second has his blouse sticking out beneath his sweater, and spikey hair, the latter version is the more rebelious of the two.
But...I think you should go a few steps further.
To go into this, I made two small images. I kinda hate paint-overs, so I just redraw it in my own style to give you an idea. But I kept them quite simple, with as little detail as possible. The first (left) is the way his parents want him to look; perfect in his school uniform. The second (right) is his adaptation to the uniform; allowing the rebel to come out.
The way I thought about it when I drew it was like this: His parents (and from the information of the website especially his mother) have quite an influence on Jacob (they can make him study something he doesn't want to do, they force him to travel through time...etc); so he will probably leave his home (at his parents'?) dressed tidy and neat in a perfectly ironed school uniform (left image below...I gave him a jacket rather than a sweater...personal preference). But as soon as he's out of sight at the first corner, he'll do several things to get the rebelious look...small things: he's still bound to the uniform. Now is I were Jacob these would be: opening the top button on his blouse and untightning the tie. Go through my hair with my hand to make it a little wilder. Pull my blouse out of my pants, and - slightly back to the 80's - roll up my sleeves (right image).
I kept his stance the same for both versions...this was to highlight the differences in the way he wears his clothing. But normally I'd have the left one straighten a little more, and the right one loosen it up a little more...
Oh, and before I forget: please put the school-logo back to the sweater (your original version had it), and re-introduce the tie you used to have; in the current version it's a little unclear that it's his uniform. Also...personally, I'd loose the shades. But that might have to do with the fact that I like to animate/draw the eyes and eyebrows. Might make him less cool, but what he looses in coolness, he will gain in character.
I hope some of the things I wrote are usefull to you, and good luck in developing the game,
Misj'
