Coincidentally I’ve lately been re-reading a lot of Gordon Korman (and reading books I missed in my youth). What is interesting is that in his 80’s opus a lot of more modern technology is just not there, which makes it much more subtle from a plot perspective. It’s not as if he’s got references to dead technology like fax machines that really takes you out of the flow of the story. Of course in a modern setting a lot of the kids in his books would probably be Pavlovianly-glued to screens, but I don’t think it’s a horrible thing to expose children to things they might otherwise be doing without a cell phone in hand.
There are only a few places where there are now seeming plot holes where a cell phone would have made all the difference (example: Artie Geller going missing in No Coins, Please!), but they’re generally so well told and so funny that I’m more than willing to suspend my disbelief.
In A Semester in the Life of a Garbage Bag where energy technology figures relatively prominently, it still reads really well, particularly because we’ve still got those types of technology problems. Even the computer teacher quitting when the computers crash and don’t save work because of power issues at school reads well in a modern context. Of course, this book is set on Long Island, so it might not have the Canadian “representation” that you’re looking to recommend to them.
I’ve only made my way through a couple of the Macdonald Hall series, but those are just good clean prankster fun, so modern technology doesn’t seem to have factored in for me. While most of Korman’s work (at least that I’ve read thus far) is very male-centered, these particular books have some good female representation and depict the girls at the school across the street as very modern and on a generally equal footing with boys, particularly with the antiquated, dotty, old-school head mistress as a foil. On this front, I’d give Korman very high marks in comparison with other relatively recent juvenile literature classics like Beverly Cleary who even through the 70’s was having main characters like Henry regularly say overtly sexist things like “Beezus is pretty smart–for a girl.”
The tough part of more modern juvenile literature is that a lot of it has gone much further upstream and spread out considerably compared to what we had available in our youths. There’s a huge swath of YA work that has filled in but which borders more on soft-core Danielle Steele a la the Twilight Series. Almost all of these are also written as parts of longer series of 3, 4, 7, or more books too, which can be annoying because the plot is often strung out in choppy ways. If they’re a bit older and in high school, perhaps John Green’s work may be appropriate?
If they haven’t come across them, I always like to recommend Holes by Louis Sachar; The Westing Game by Ellen Raskin; From the Mixed-Up Files of Mrs. Basil E. Frankweiler by E.L. Konigsburg; Lois Lowry’s The Giver (et al.) which I’ve been re-reading lately too; and Ender’s Game by Orson Scott Card. All of these are generally great timeless literature, and I often recommend them to adults who may have missed them.
I’m also a fan of the more recent Mysterious Benedict Society series by Trenton Lee Stewart which has some of the rollicking fun of Korman with some interesting twists, plotting, and has some well-rounded representation of characters.
A while back I read the first in a series of steampunk/pirate books called A Riddle in Ruby by Kent Davis which had a lot of interesting science, alchemy, science fiction, and adventure. While it wasn’t quite my cup of tea, it was pretty well done, entertaining, and may appeal to them.
Also similar to Korman, but even older to the point that they read as period literature, they might find The Great Brain series by John D. Fitzgerald or The Mad Scientists’ Club by Bertrand R. Brinley highly engaging. Sadly, while entertaining and with a lot of heart and cultural intelligence, they don’t have much, if any, female representation, primarily as a function of their authors and when they were written.