For a lefty (which I’m not), look at the GSR. My nephew has (had?) a lefty GSR in .308. Shot and handled nicely.
Marlin lever guns can be lefty-friendly. I have no experience with the Savage 99, but where I am, the few that I see are pricey.
In terms of caliber, I think it depends on what you want the gun to do for you. One of the reasons I would stick with a traditional lever action caliber is that, at least here, they are fairly plentiful and not too expensive. Yeah, .30-30 is more per round than .223, but it’s not bad and whenever there’s talk of a magazine or gun ban, the calibers that are associated with those items get scarce. This is one of the reasons I never picked up a GSR. Great idea for a low profile nearly ban-proof gun, but the ammo they use is ban-susceptible and prone to going scarce. Now if they made one in .270 or .30-06 with available magazines, I’d be interested. I know they made one in 6.5 creedmoor, but I don’t see the point for that platform.
While I don’t know your particular situation in Canada or your desire or intended use for a lever action, consider ammo availability.