Okay just rewatched the first scene of S05E01 on Netflix, he does do the 52 in the bacon, but 1) we have no sense of how far in the future it is, only that it's in the future, and 2) the date matches the date on his fake ID that he shows the waitress, there is no evidence that it is the same birthday as his real birthday. What there is evidence of is that he buys a big ass gun with no explanation as to why. Clearly he's about to have some kind of a showdown, he could easily die in the final episode of series.
As stated, episodes (roughly) 1-45 were his ages 50-51.
From my point-of-view, I don't think he dies or goes to jail.
It isn't concrete evidence, but it suggests that.
You're right in that the only flash-forward we've seen is him doing his weekly shenanigans.
But I doubt they'd be able to go from 51-52 in the final 8 episodes, however, it is possible.
But VERY unlikely.
It is very rare that any series ends with the protagonist dying, but if there is one to do it, either of these two would certainly be at the top of my list. Either way, you are absolutely fooling yourself if you think that the first scene is any indication that he lives; just like in the first season with the foreshadowing with the pool, the plot line will definitely coincide with the flashforward before it's all said and done. Even if you're right that the timing is off, he could have intentionally done the 52 on the birthday of his fake ID for the purpose of having an alibi for something else, or any number of other reasons. It is honestly MORE unlikely that his fake ID birthday is the same as his real birthday than him dying.
In any case, I appreciate the discussion; can't wait for the final eight episodes!
@Mooshire
Nothing has killed either bet yet...