I think your friend is on the right track, although you might find that Batman, like most superheroes, has so much history, with false starts, do-overs, and epic stories that hinge on bits of continuity ephemera, you might get frustrated easily. Superhero stories work best when you’re always backtracking, and it seems like you’re exploring a tremendous cavern filled with endless possibilities, rather than going at it methodically and quickly realizing you’re walking down the same three halls of the funhouse, just with the locations of the rubber spiders and scary faces adjusted slightly.
That said: yeah, start with Year One, which is great.
But before the Long Halloween, try and get a hold of Batman: The Man Who Laughs, which is a one-shot by Ed Brubaker and Doug Mahnke about the first meeting of Batman and The Joker. It’s pretty decent and will fit in with the chono approach you’re trying.
Then, I guess, The Long Halloween, which never did much for me but I know a lot of people like. Then, the sequel, Batman: Dark Victory.
Matt Wagner has done a couple of mini-series set in Batman’s early days, based on early Bob Kane Batman stories. Batman and the Monster Men, and Batman and the Mad Monk. Those would probably work well. That should get you started.
Then there’s the middle period, which is even more all-over-the-map in terms of what’s collected and what you might like. But let’s say you should at least read (if not buy) Batman: A Death in the Family, which will has events that get mentioned a lot in later Batman stories; Batman: Hush for more fan-service by Jeph Loeb (again); and then maybe Batman/Grendel by Matt Wagner (again); Batman: Blind Justice by Sam Hamm (who co-wrote the Tim Burton Batman screenplay and does a really weird Batman story here); and a couple others which I can’t really decide on yet. (Let’s say Batman: Two Face & The Riddler, since it has a really good Riddler story by Neil Gaiman, and Batman: Arkhan Asylum: Living Hell by Dan Slott although that might be out of print.)
Then watch all of the Batman series by Warner Brothers, and the movie Batman: Mask of the Phantasm which is a loose adaptation of Batman: Year Two (and works much better, I think.)
Then, finish it up with Batman: Killing Joke by Alan Moore & Brian Bolland, and Batman: Dark Knight Returns by Miller.
That’ll probably work as a nice chrono overview, but at some point you’ll just find creators you like or a run that sounds interesting to you and you’ll steer away from this map, and you’ll be just fine.