• Problem: Jack’s compass was bartered from Tia Dalma, but in 5 he got it from a crewman. Solution: Jack did, in fact, get the compass from the crewman but later lost it at sea when Beckett sank the Pearl. It came to Tia Dalma (Calypso) who recognised its power and Jack had to later barter it from her to retrieve it.
• Problem: the Wicked Wench was shown as a pirate ship, but Jack worked for the navy (’people aren’t cargo’ scene). Solution: The Wench was a pirate ship when she was under control of the previous captain seen in 5, but when he died and she became Jack’s ship, Jack decides to join the navy and work under Beckett (he was still very young + not yet branded and probably saw it as the best thing to do). When Beckett asked Jack to ship slaves, he liberated them, got branded, etc. and the ship sank. This explains the pirate flag in 5 and also the problem of ‘Why would Beckett sink a navy ship just to get back at Jack?’ Jack goes on to make a deal with Davy Jones and you know the rest. 
• Problem: Jack is a gallant hero and very intelligent, so why was he ‘drunk’ the whole time? This one really pisses me off personally Solution: it’s been however-many years since Jack has been on sea, as we saw in one of the scenes the thing he desires most is to sail again, so it could be excused that he wishes to drown his sorrows 24/7, considering he’s no longer a ‘wanted’ or famous pirate, he doesn’t have a ship or much of a crew and his friends aren’t in contact with him. 
• Problem: Why does Will Turner have barnacle-face when we know that this only happens to those who do not fulfil their duty (i.e. Davy Jones)?  Solution: Will did not have barnacle-face up until that point. It could be assumed he was doing his job well and then noticed Henry was drowning and stopped ferrying the dead in order to save him, i.e. as soon as he ‘crossed-over’ he gained the barnacles. This would explain why Will only had a few barnacles and not ‘transformed’ like Jones.
• Problem: Why is Elizabeth in a dress and corset when the whole point of the first movie was freeing her from it? AARGH I hate this one aswell, completely undermines Elizabeth. Oh well. Solution: Elizabeth felt it necessary to return to civilization to raise Henry, she did not want him involved in piracy for his own good and therefore didn’t talk about Jack. At the time, a woman such as Elizabeth would have been known in civilized culture as ‘governor’s daughter’ rather than ‘pirate king’, so she has to live up to this name in order to be accepted in that society (remember we’re talking 18th century here). She doesn’t have her husband, Jack or even mentor!Barbossa to help ‘free her’ from these expectations
• EDITED Problem: When, in the time between being cursed, dead, looking for Jack, joining the navy and controlling the ocean did Barbossa have time to have a wife and child? Solution: After the events of AWE,  he had Smyth as a wife, who later became pregnant and died in childbirth, afraid that Carina would be worse off as a pirate girl, and, of course, out of a sense of his merciful nature caring dad!Barbossa left Carina at the orphanage. Barbossa then joins the navy. (thanks to everyone who pointed out my mistake)

jack sparrow [ a summary ]

                               you handle your own when you become a man                                                                      &                                become  a  man  when  you  handle  your  own.

30 Days of Pirates of the Caribbean

Day Ten. A quote from “At World’s End”

Isla de Muerta, remember? You shot me.