Lots of timing question and card helping. I have tried FAQ but could not find these answers.

1) On Jake pilot skill gets a free barrel roll or boost, this means can he do two of them? I know in the rule book it says that you can only do an action once but Jake ability says free action. So to me this means he does not have to "use" it as my action. So Jake free barrel roll, two straight, barrel roll as action: is this allowable?

2) I am sure this has been answered many times before, Outrider title makes what ever secondary weapon now the primary so when I get the lose a secondary weapon I still have my Outrider canon. Example is the HLC. Same thing as gunner, can gunner be used on the turret of an Outrider?

3) What is the timing of Bossk crew and gunner? Does Bossk's ability activate and is then usable for the gunners attack?

4) What is the timing of decloaking and intelligence agent? Which happens first? I had some trouble with this during a game at my last OP tournament.

1) No. A free action is still an action, just one that is done outside of your normal action step. You still cannot violate the "once per round" rule.

2) The Outrider title does not make your secondary weapon your primary; it locks out your primary weapon and forces you to use the cannon. It is still a secondary weapon for all purposes, which means Gunner does not work.

3) The timing is the same, so you may choose the order of resolution. Bossk first is strongly advised.

4) Decloaking is specifically ruled to happen dead last of all "At the start of the Activation phase" effects. Intelligence Agent must go first.

4) Decloaking is specifically ruled to happen dead last of all "At the start of the Activation phase" effects. Intelligence Agent must go first.

This is more important for ships that contain both these abilities than having them separated between yourself and an enemy.

On a Tie Phantom - Allowing the IA to perform first gives you the intelligence to decide which way you will decloak (the IA would be fairly useless if it had to occur last)

2) I am sure this has been answered many times before, Outrider title makes what ever secondary weapon now the primary so when I get the lose a secondary weapon I still have my Outrider canon. Example is the HLC. Same thing as gunner, can gunner be used on the turret of an Outrider?

You clearly did not read the card, or you read it as you wish it was...

This is integral text from the card: "you cannot perform primary weapon attacks"

I wonder how this got translated to my secondary weapon is now a primary weapon...

Also no where on the card is it said that your secondary weapon upgrade card are now primary weapon upgrade card. So you will have to discard it.

1) On Jake pilot skill gets a free barrel roll or boost, this means can he do two of them? I know in the rule book it says that you can only do an action once but Jake ability says free action. So to me this means he does not have to "use" it as my action. So Jake free barrel roll, two straight, barrel roll as action: is this allowable?

In addition to the fact that free actions don't let you violate the rule against performing the same action more than once per round, Jake doesn't actually have the Barrel Roll action. The only way he can perform a Barrel Roll is via his pilot ability.