Crackerjack [base class]

[Realms of Chaos]

2) Contemplation is really underpowered. It's basically a Rage, but to stats that are suboptimal to combat. I suppose some ranged weapon cheese may be possible, but as it's basically an untyped +2 bonus to two ability scores (not STR or CON) for a limited time, it seems rather lame. During this time, you're only slightly better at certain things than you are normally, & few of them are applicable to your primary occupation of killing things & taking their stuff. It needs to be buffed before I'd consider taking a dip, let alone taking this all the way to level 20.

...

4) More Skill Mastery features should be added, so that the 'Jack isn't just a one-trick pony. I mean, these two features are cool, but they top out at level 9, & are never seen again. A total of 3 or 4 Ultimate Masteries wouldn't be overpowered.

I think I know a way to fix problems 1 and 4 simultaneously. Why not have Contemplation, in addition to granting ability bonuses, grant a +4 competence bonus to all skill checks relying on one of those abilities.
When you gain intense contemplation, you gain the benefits of skill intensity mastery for all such skills.
When you gain ultimate contemplation, you gain the benefits of ultimate skill intensity for all such skills.

...well, it's a start, anyway.

Also, perhaps give this thing trapfinding at 1st level (as that is the one ability expected of all skill monkeys). Unless, you know, you're afraid of this looking too much like the factotum.

The thing about this class is that I get the impression that it is bad at combat by design. This is the guy that guides you to the kobold lair, notices the kobold ambush to warn you, and parlays with the warchief to get a fight between one of you and their strongest warrior.

I can honestly say that I haven't seen many classes like this. Other than using diplomacy/bluff (or clever feat selection), this guy really has no way to remove enemies from combat.
To put that in perspective, even characters with vow of peace gain an aura that calms emotions (removing characters from combat). Building a class that takes care of things between combats is an interesting concept but it ultimately fails.
As campaigns move onwards, they run into problems that require magical answers. Flooded dungeons need exploring, Flying cities need to be reached, and vast distances need to be crossed within an hour to stop impending doom. Use Magic Device is no substitute for the ability to solve a problem yourself, alas.
This guy has a bit of utility but take note that several other "utility classes" like the bard and factotum have a bit of magic. Also note that the bard is considered less than useful and the factotum only enjoys its fame due to the existance of a single feat that easily breaks it.

On the other hand, this class may be far too powerful in a gestalt game as this class complements just about anything.

Wizard/Crackerjack: Both rely on Int. Contemplation boost spell DCs. Far more skills and skill points. Gives wizard good Reflex save, higher HD, and more BAB. Gives the unarmored wizard +5 AC and all of the bonus feats that it could ever possibly desire.

Fighter/Crackerjack: Even without high Int, Crackerjack gives more skills and skill points to the fighter. Gives the Fighter two more good saves, makes builds with lighter armor more feasible, and 30 bonus feats is likely enough to complete every masterful fighter build out there.

If this class were just on its own, raising the skills or giving some minor spellcasting (on par with a ranger or paladin) might be in order. I'm afraid to recommend it, however, because that makes gestalt even more broken.