Several reasons are speculated for why the attack happened on April 20. A smart person can think any one of them. But I want to go through them and then conclude with what seems to me most likely:
Hitler's birthday is the most infamous. But did anybody know that was Hitler's birthday before the attack? It seems the attack is why people know that, meaning the perps would not have known that. Indeed, for true, card-carrying the Nazis, the date viewed with most reverence is November 9, the date of the Beer Hall Putsch, rather than the birthday of the Fuehrer.
Supposedly, they said April 19 was going to be the date for the attack. The evidence for this is interpretation of the Basement Tapes, saying it's "7 and 1/3 days" on April 11. It seems a little flimsy, given we haven't seen them, I have to wonder if the viewer or the perps math was off. But I will take it for granted. April 19th is:
1775, the day of Lexington and Concord. Columbine's fight name is the Rebels, as in Revolutionary War rebels. Eric said we needed to kickstart the revolution.
1993, Waco burning
1995, the Oklahoma City Bombing, due to the prior two dates.
There's also how 4/20 is the day for weed, and similarly a day for "senior pranks". As others have remarked, kids are holding up 420 in the senior photo. Also, while cannabis and the perps are not often mentioned together, it seems that's because we are relying on figures like their parents rather than their friends. Dylan's brother was supposedly kicked out for smoking pot, and Eric's "Berserk" was his weed pipe he kept in his pocket. They weren't shy about cigarettes and booze.
However, on those same Basement Tape transcripts, Eric says he's wondering whether to do the attack "before or after prom". That means the week before the attack was in play as well - the prom was the prior weekend. That means they entertained doing the attack on any of April 12, 13, 14, 15, 16, 19, 20, 21, 22, or 23.
In fact, in all of their writings, they are committed to "April" from early on, and are no more specific than "Some time in April" Eric says in NBK.doc "The holy April morning of NBK" says Dylan. "Heh, get this. KMFDM’s new album’s entitled “Adios” and its release date is in April." says Eric, and so on. And if it was to wait as long as possible to plan or whatever, they could have attacked in May.
So what was in April, but before the 12th through the 23rd? Of course, Eric's 18th birthday on April 9.
In NBK.doc, Eric is not even sure they would be able to get guns. That seems the obvious reason in retrospect.
Imagine they never got Robyn to vouch for them at the Tanner gun show. When would they have gotten the guns then? They would have had to wait until Eric was 18. That's a far more practical reason. That's where I cast my lots for why April.
And of course, if that is right, that shows birthdays were on their mind, which comes full circle by bringing back up Hitler's birthday.