What genereation is Smiling Jack?

The most powerful vampire that you meet in Bloodlines
and everybody hardly realises that, it's Caine, he certainly knows
how to lay low. If anybody is still sceptic, read the novel:
Vampire: The Masquerade - Gehenna: The Final Night to confirm that.
The Malkavian also learns and says more things about the Dark Father.

About Generations and power, just see to LaCroix, he lived about 200 years
and the Discipline he mostly mastered was Dominate,
he didn't improve his fighting skills and other Disciplines,
whilst your character was sent to the front line and suicide missions
(because LaCroix wanted your character to die) several times,
and learned a lot of things, then it mastered Disciplines and its power,
Thanks to its (your) skills, it was able to survive.

The Nosferatu have complicated unlives, so they have to learn a lot of things
if they want to survive, being that Gary was the Nosferatu Primogen,
he certainly did well all those decades. If you play with a Toreador,
Gary won't scare you, though you might feel uncomfortable by the discussion,
he makes fun of you, insults you and wants you to suffer, you can do that too,
after his humoristic "boo" when he appears, you can insult him, then he reacts,
atmosphere feels heavy all time, his laugh and twisted humour pacifies that.

Jack is a Brujah who's usually causing anarchy, unlike other Brujah
that spend their time complaining and fighting after being provoked,
Jack makes plans and he was always at first row, not just watching,
even fighting and politicking, not in the traditional way though,
he likes to overthrow Princes, encouraging Caitiffs and others for his cause,
hmm, I can't remember where else that happened... (VTMB tutorial)

Well, that's what the Anarchs do, they manipulate others with their words
and they give nothing, you can see they do that in VTMB too,
Damsel: "I hate LaCroix... there's an epidemic... Do something",
Skelter: "Camarilla poster child... Oh, Masquerade... there's a noisy Ghoul".
Nines Rodriguez was the only one who made many things for you
and he didn't want anything in exchange, but if you reject his cause,
he'd have no problems to kill you. Well, after all,
nobody is good in Vampire: The Masquerade, they're all monsters.