I imagine using the winch to travel along the rope would be similar to using a move action to climb (Granted you can literally pull your own weight). Since no action is given to retracting the rope, It's likely in GM territory. I would recommend ruling it as a move action as well, for simplicity.
Since I doubt it's an automated/powered winch, and more likely just a hand crank, then no, you probably don't automatically pull the creature towards you. Sadly, it's not a Hookshot.
Since you are using ammunition with the grapple weapon property...
Grapple: On a successful critical hit with a weapon of this type, you can grapple the target of the attack. The wielder can then attempt a combat maneuver check to grapple his opponent as a free action. This grapple attempt does not provoke an attack of opportunity from the creature you are attempting to grapple if that creature is not threatening you. While you grapple the target with a grappling weapon, you can only move or damage the creature on your turn. You are still considered grappled, though you do not have to be adjacent to the creature to continue the grapple. If you move far enough away to be out of the weapon's reach, you end the grapple with that action.
In all likeliness, if the opponent breaks free, you're simply left with a barbed bolt attached to a silk rope left limp on the ground, attached to your crossbow's winch. There's no mention of you being unable to end the grapple (if you are the one in control), so go right ahead and end it as normal(Free action). If they successfully take over, I see no reason for them not to yank you right back.
Once the grapple is broken and the bolt lay on the ground, there's no mention of this penalizing your ability to attack with the weapon, so you can probably just keep right on shooting at that point.
That's my take on it.
EDIT:
1) Since it says earlier that its a full round action to wind 50 feet of since rope onto winch, I would say it still a full round action to retrieve the rope, provoking just like winding the full length of rope. And so far as pull herself along part, treat it as climbing a rope, its still possible to fall by loosing your grip on the winch handle.
That's true. My bad. Loading the rope is a full-round, so winding it back up will likely be the same. my bad.
1: it says " After firing such a bolt, the wielder can use the winch to retract the rope or pull herself along the rope if the bolt is secure."
which i believe implies as part of the attack action(which is itself a standard action).
2: neither, you probably fail to rotate the winch. you know, you try to rotate it but you'll lose grasp of the crossbow before the target moves so you simply fail.
3: it's a move action to retrieve an item. if the item is attended it;s a steal action.
?4?: so here's the thing I looked up barbed and grappling bolts.
there are only barbed bolts, and these give you the grapple condition to your bolt
Grapple: On a successful critical hit with a weapon of this type, you can grapple the target of the attack. The wielder can then attempt a combat maneuver check to grapple his opponent as a free action. This grapple attempt does not provoke an attack of opportunity from the creature you are attempting to grapple if that creature is not threatening you. While you grapple the target with a grappling weapon, you can only move or damage the creature on your turn. You are still considered grappled, though you do not have to be adjacent to the creature to continue the grapple. If you move far enough away to be out of the weapon’s reach, you end the grapple with that action.
Arrow/Bolt, Barbed
The head of a barbed arrow resembles that of a harpoon.
Benefit(s) When a barbed arrow is attached to a length of silk rope and fired from a bow, the arrow's range increment is reduced to 30 feet, but it gains the grapple special weapon quality.
Barbed bolts exist for crossbows.
this means you can only use it on people 30 feet away, and as per grapple rules you can end a grapple as a free action. however, you count as grappled, so that means you're using your hands to keep control of the opponent and thus take a -4 to your grapple check unless you drop your crossbow. which i find weird, since you're winching them...
Humanoid creatures without two free hands attempting to grapple a foe take a –4 penalty on the combat maneuver roll.
also you only pull them to you if you succeed on the grapple check, but the grappled weapon condition appears to overwrite this, saying it's not required for them to be adjacent, however, I guess you gain a +2 when you do attempt to do so.
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1: If the bolt isn't attached to anything then retracting the rope is a full round action. If using it to climb then follow the climbing rules.
2: The crank crossbow is just adding +2 to the grapple attempt. The rules for barbed arrows/bolts say to use the standard grapple weapon quality;
On a successful critical hit with a weapon of this type, you can grapple the target of the attack. The wielder can then attempt a combat maneuver check to grapple his opponent as a free action. This grapple attempt does not provoke an attack of opportunity from the creature you are attempting to grapple if that creature is not threatening you. While you grapple the target with a grappling weapon, you can only move or damage the creature on your turn. You are still considered grappled, though you do not have to be adjacent to the creature to continue the grapple. If you move far enough away to be out of the weapon's reach, you end the grapple with that action.
3: Bolts which hit are assumed to be broken. Thus, it likely isn't so much a matter of removing the remains of the bolt as freeing the rope. If there is no grapple opportunity, or the grapple attempt is defeated, then I'd rule that you can just retract the rope normally (full round action). Otherwise, you would need to give up or end the grapple opportunity (free action) first.
1: it says " After firing such a bolt, the wielder can use the winch to retract the rope or pull herself along the rope if the bolt is secure."
which i believe implies as part of the attack action(which is itself a standard action).
I strongly doubt they'd invent a weapon that'd let you literally pull and crank yourself 50ft as standard action in any direction without any other skill check. Thus, I recommend using climb rules instead, and a full-round action at the least to fully retract the rope as others suggested.