I always enjoyed https://tomenet.eu/ !
As most roguelikes it takes a little time to get into it, but it's really worth the effort (especially playing together with a friend).
It's got a quite small but friendly community and should run under Mac OS (opensource)!
Not exactly roguelikes, but MUDs [1] are multiplayer games with a roguelike feel, but they are more like the ancestors of MMORPGs, TBH.
A telnet program should basically be enough to start playing. There are some "MUD client" programs that enhance the interface (dunno about MAC OS), and some sites offer enhanced web interfaces as well.
One of the most popular, Aardwolf [2] is very newbie-friendly.
Thanks, I am old enough to know of MUDs "first hand". But what I am looking for is a way to play casually with exactly one friend (who lives hundreds of Kms. from me) and not to spend more than 1 hour in the game at the time.
Replying to myself in case this could be of interest to someone else.
After a long debate I convinced my friend to try Torchlight 2.
We played for maybe 90 minutes yesterday and so far it seems to be at least ok for both of us.
We used Discord voice chat to coordinate.
(I think it can scale to up to 4 different cooperative players - of course it is not turn based but from my previous experience with Torchlight first edition I think it is playable even if your reflexes are just average).
Torchlight, and really all diablo-likes, has the problem of being too simple/easy, with higher difficulties primarily item-gated more than whatever skill/strategy; its long term value comes from multiplayer + grinding/trading qualities of random drops, and less so from well, playing it as-is.
As a result, they've never really satisfied my roguelike itch tbh.
Also, if that multiplayer + grind/trade/build characters + sets is the main value you get from Torchlight, then probably consider path of exile, which pretty much optimizes purely on the multiplayer aspects of Diablo 2 (Torchlight lacks some purpose imo; they set out to do a better Diablo 2, but didn't really pick a place to optimize, and didn't do well enough at optimizing everything, and didn't really remove any fundamental flaws)
I agree with your description. Torchlight II was a compromise - The original idea was to play Divinity Original Sins but I pushed us towards a simpler (and less expensive) game because I suspect neither of us would be able to devote enough mental effort and/or sustain interest for a long time.
If my suspect is wrong, we will try to move on to something more complex.
Mac OS would be a plus because both me and my friend use mostly Apple stuff at home.