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Bruce meets Jason for the first time on the anniversary of his parent's death¹. This is either June 26 or late November (I can't remember the exact date unfortunately) depending on whether you use pre- or post-Crisis continuity. I generally prefer the June 26 date, if only because according to Nightwing (1995) #1, the Graysons fell on June 27 and I find that darkly humorous, but that's the pre-Crisis date so we're going to use November instead.

Jason is then in training for six months before officially becoming Robin². This puts us in May for his Robin debut. However old Jason was when he met Bruce is how old he is here, because Jason has only ever had one birthday no matter the continuity, and that date is August 16³.

How old was that? Not certain. It depends how you treat the letter columns. In the back of Batman #413, Dennis O'Neil says that Jason is 12. There is a question to be asked about whether that means he's 12 in Batman #413 or if he's 12 in his origin story in Batman #408-409, which is what the letter was written in response to. Now, Batman #413 takes place during the school year, which most likely means that his birthday has passed since he became Robin⁴. If he was 12 in his origin, he would now be 13; if he's 12 in Batman #413, he would've been 11 when he became Robin.

However! If you go back one issue to the letter column of Batman #412, you'll find that O'Neil says that Batman #408-409 take place ~3 years ago. If we take that as canon, that means that if Jason is 12 in Batman #413, he was 9 when he met Bruce and still 9 when he became Robin. If, however, he was meant to be 12 in his origin, that means that Jason in Batman #413 is 15. Given the emphasis on Jason being "The Boy Wonder" on multiple occasions, and the fact that this is distinct from Dick, who had grown into "The Teen Wonder" as he got into his teen years, I think it's safe to conclude that if both of these bits of letter column lore are canon, Jason has to be 12 in Batman #413 and 9 in Batman #408.

Now, I take a bit of issue with the "three years" bit, because Dick later says that he left home two years ago⁵. Personally, when it comes to canon hierarchy, I take what's in the comic itself as canon over letter columns. However, this still leaves Jason at 14 in Batman #413 or 10 in Batman #408.

At this point, I turn to Batman Annual #12, which establishes that Jason is in 7th grade. 7th graders are, barring being held back or skipping a grade, 12 turning 13, and a major thing we know about Jason is that he's smart. He's really smart, he's very quick to learn, and he did well in school, all of which leads me to believe that he wouldn't have been held back, which further confirms that he was 12 in Batman #413 and thus 10 in Batman #408/when he became Robin.

Jason is mentioned to have dropped out of fifth grade⁶. Given that fifth graders are 10-11, the fact that Catherine died in February⁷, and Jason saying that she was sick for over a year, I think we can conclude that he didn't drop out of school until Catherine was dead. And, because he has to be 10 in Batman #408, we have to conclude that he is a) finished fourth grade after his mom died and b) one of the youngest kids in his grade. This makes him 12 for his entire 7th grade year, ergo he's 12 in Batman Annual #12.

Batman Annual #12 came out six months before the first part of A Death in the Family. Because the annual mentions report cards coming up, I'm guessing that this takes place in either December/January (midterm) or May/June (end of school), depending on when exactly school gets out. The principal says that the grades are better than last year's, which to me indicates that this is probably closer to the end of school with the summer dates. Jason mentions the KGBeast as well, and Batman #420 came out the same month as the annual, so we know it's after Ten Nights of the Beast.

When is Ten Nights of the Beast? Well, I went on a whole side quest trying to figure it out using sunrise times and entirely too many calculators. My best guess is March or April, but it's never really confirmed. The fact that Batman #423 has a sunrise around 6 AM also indicates that we're in the first half of the year. All this really does make me feel more confident in saying that Batman Annual #12 takes place near the end of the school year.

After a quick reread of the last couple issues leading up to A Death in the Family, I'm fairly confident in saying that there's no mention of a specific date before Jason's death. Traditionally he's said to have died on April 27, which is a clever reference to the fact that the infamous poll was in Batman #427. However, reviewing the lead-up to DitF as well as later issues, I personally believe Jason died in July.

So to summarize:

Jason is 10 years old when Bruce meets him in late November

He becomes Robin six months later, still age 10

He is 12 for most if not all of his post-Crisis run, with an implied year or so between his debut and our exit from flashbacks in Batman #412

Jason is killed in July, just one month short of turning 13

And that's it! I'm so sorry for. um. everything about this. I kinda ended up breaking down my usual timeline to keep everything post-Crisis and had to rebuild it from scratch, but hey, at least it's done now! Do I think DC has thought through any of this at all? No. Will I be changing any of my personal projects to suit this actual, fully-canon timeline? No. But now we know better and going forward, we can use this. Sorry for rambling so much, hopefully this was helpful :)

References

¹ Batman (1940) #408

² Batman (1940) #410

³ Detective Comics (1937) #790

⁴ This is because Batman #408-409 and probably Batman #410-411 are meant to be flashbacks; nothing is ever really brought up, but presumably Jason's pre-Crisis Robin run is meant to be altered by the Crisis and fit in here, with Batman #410-411 taking the place of Batman #368 and Detective Comics #535 as his first outing as Robin. Batman #401-403 also slot in here somewhere, seeing as they're post-Crisis but released before Jason's updated origin.

⁵ Batman (1940) #436

⁶ Batman (1940) #410