1. When Paragon shoots at ship that you have already attacked this turn it adds one black die to its attack pool. Is this regardless of range? Can an activated fighter squadron fulfill this condition?
2. When you fire at an Objective ship (see Most Wanted Objective Card), you can add one die of any color that is already in your pool. Does this mean that the Paragon could then add a second black die to its attack if the previous condition had already been met?

Yes times two.

1. When Paragon shoots at ship that you have already attacked this turn it adds one black die to its attack pool. Is this regardless of range? Can an activated fighter squadron fulfill this condition?

Yes, it is regardless of range. No, an activated squadron cannot fulfill the condition. The reason being, the word "you" in Paragon's text specifically refers to the ship that upgrade card is attached to. Since Paragon is attached to an Assault Frigate, squadrons cannot fulfill the condition (and squadrons cannot take upgrades anyway — not yet, at least). Also, it must be Paragon itself that makes the second attack in order to get the extra attack die. The "you" term refers to that specific ship, so if another ship attacks a target vessel before Paragon, that does not mean anything.

In other words, Paragon needs to get two arcs of fire on a target ship in order to pull off the bonus attack die. This is not always as easy as it sounds...

Yes, it does. You could also manage to add a third black attack die if Paragon had a Concentrate Firepower order dial revealed for that turn. Showing my work:

Paragon makes its first attack against the Objective ship, hopefully with its front or rear arc, adding one die because the target is the Objective ship.

Paragon makes its second attack against the Objective ship, this time with a broadside.

— During the Gather Dice step, Paragon would assemble whatever dice it has for its broadside (a basic set of three red dice and one blue — plus maybe another red die if you have Enhanced Armaments attached)

— Because this is the second attack made by Paragon against the same target, you may add a black die because of Paragon's ability

— Because the target is the Objective ship, you may add another black die to the attack dice pool

— You roll your attack dice pool, and if your command dial is Concentrate Firepower, you may add a third black die and roll that.

That's all more or less correct, however you would roll your initial attack dice first (the dice printed on the broadside arc of the ship). All the other dice are rolled in the modify dice step.

This means you can see what your initial dice roll then decide what colour dice you want to roll for most wanted. If you use the Paragon ability first in the modify dice step it would add a black dice to the pool allowing you to roll addition black dice with most wanted. However if your initial d8ce don't include any accuracy tokens you may find it better rolling blue to make sure he can't use certain defence tokens such as brace.

As a side note enchanced armament increases side attacks of a side by 1 red die. This increases the printed value and is rolled with the initial pool as it's not an add effect.

Yup important points there regarding dice rolled initially and when you roll "added" dice.

regarding your first question - the "you" on the card refers to Paragon itself

So read it like this: when Paragon attacks a ship that Paragon has already attacked this turn...

therefore squadron's activated by it don't count as they are themselves attacking.

I took it as you the player has attacked that ship. So i was having my neb b hit it 1st theb the assault frig would fire on it with the bkack dice.

So sounds like ffg should change the wording to you may added a black dice for your second attack on the same target.

I took it as you the player has attacked that ship. So i was having my neb b hit it 1st theb the assault frig would fire on it with the bkack dice.

So sounds like ffg should change the wording to you may added a black dice for your second attack on the same target.

The rulebook is quite explicit that anytime a card says "you" it is referring to the ship the card is equipped on.

I took it as you the player has attacked that ship. So i was having my neb b hit it 1st theb the assault frig would fire on it with the bkack dice.

So sounds like ffg should change the wording to you may added a black dice for your second attack on the same target.

The rulebook is quite explicit that anytime a card says "you" it is referring to the ship the card is equipped on.

Yup, no wording change needed at all, every card that uses 'you' is explicitly referring the ship itself. Its in the rules, nice and simple.