1994 - Catch-22

Ok so at the end this is where Desmond met Penny.

In Flashes before your Eyes is said in a podcast that we should believe that the year is 1996..

The bottle of wine has the date 1995, but I have heard that is when it is barreled, if I am wrong please correct me..

It is also said in Flashes before your Eyes that Desmond and Penny have been to together for 2 years... Desmond tells Whitmore this when he is in the interview..

This means that when they met it was 1994 or earlier.. Does this sound correct to all of you.. I want to make a timeline for Desmond..

Thank You!!

I tip my crown to you, wenighter, as you are the Research Queen! A single unified timeline for Desmond might prove more difficult than you expect.

Thanks Queen, I'm getting closer =)

In this episode Ruth (the chick Des was going to marry) said he had not had any kind of religous experiance since some team won 5-27-95 According to Lostpedia...

The vintage of the wine bottles and Ruth's mention of Celtic winning the Cup date this flashback to 1995, where he first meets Penny. Desmond's later flashback where he breaks up with Penny takes place in 1996. Normally wine is dated based on the date of the grape harvest, and Cabernet Sauvignon is usually aged in barrels for years before being released, so the date on the bottle is likely a production error meant to show the date of the flashback and not a realistic vintage date.

So I am having trouble figuring out what the timeline is here or if there is a flaw in the time line..
Here is was Lostpedia had to say about the year..

Normally wine is dated based on the date of the grape harvest, and Cabernet Sauvignon is usually aged in barrels for years before being released, so the date on the bottle is likely a production error meant to show the date of the flashback and not a realistic vintage date.

This if it was not a production error would push the date a head more.. So please help if you can... I'm just getting myself so confused right now....

So tonight I rewatched Live Together Die Alone...

[We see Desmond in the hatch, holding a gun. He's finishes off a bottle of booze, and opens the Dickens book. A letter slips out. We hear a VO of Penelope reading the letter.]
PENELOPE: Dearest Des, I am writing this letter to you as you leave for prison. And I've hidden in the one place you would turn to in a moment of great desperation. I know you go away with the weight of what happened on your shoulders. And I know the only person who can ever take it off is you. Please don't give up, Des. Because all we really need to survive is one person who truly loves us. And you have her. I will wait for you. Always. I love you, Pen.
[Desmond sobs and throws the bottle.]

Remember when he reads this.. She said that she wrote it as he was leaving for prison. Well that would have to mean in Desmonds flashback they never broke up. Wouldn't it? Something just doesn't add up here for me if what all happened in Flashes Before Your Eyes took place in 1996.. Help what do you think?