I generally find the hardest truism for modern liberals to accept is that neutral policies reinforce existing power structures through their own inaction. I sort of take this as the core premise of white privilege.
A bit vague and trolly, but I'll buy the argument that gerrymandering is not inherently evil, it's just generally abused. Don't hate the game, hate the player, as it were.
I think my gripes could be summed up:
1) Gerrymandering is a small part of the larger problem with electoral politics where people look are constantly for ways to game system in acceptable ways. If it becomes acceptable to blatantly manipulate the system for the purpose of enfranchising people, then it becomes equally possible to use the system to disenfranchise people once the system comes under duress. I prefer to keep as much of the underlying machinery of the electoral system out of the hands of politicians as possible.
2) The difficulties in the state deciding which cultural or social groups are at a disadvantage. Yes, there are groups which have been historically disadvantaged and who could clearly use a "hand up", but not all decisions are nearly so obvious. Which form of presumptuous privilege is worse?: The ethically/socially dominant group maintaining power by relying on artificial boundaries (arbitrary geographic blocks), or the dominant group deciding which groups will be represented? What do you do when you have two seats and a three-way split (a pure construct for the sake of argument, but not a crazy one I think)?
3) I think we both agree that Gerrymandering plays to the incumbents. Do you think that's all that great?
Clear rules (probably tied to population percentages) go a long way to resolving these issues, but that's not the way things are calculated now in the US, since this is something done in the legislature.
By comparison, we have an independent arm-length electoral body whose sole role is to to redistricting based entirely on census data (along with other basic stuff like voter registration, etc.), which has resulted in the solution you're looking for with a lot less meddling and a lot fewer geographical absurdities. Which is to say, we do in fact have gerrymandering in modern Parliamentary systems, but it's far less egregious and very little of it is politicized, because the process has been very deliberately isolated from the party political system (at least in Canada and the UK... I don't know about the other dominions yet).
I actually was unaware of the extent that we Gerrymander in Canada, because our ridings tend to be very geographically clean and don't look anything like the districts in the linked article, but I'm actually quite happy with the situation.
My original premise was basically "We can't trust people in charge not to try and abuse this, so let's just ban it", but it happens everywhere. So I guess this is more of a critique of the American system than anything else. Since we have working examples of functional gerrymandering to good effect, I really can't argue against the root concept so much as the way it was implemented stateside.
Perhaps you disagree that Gerrymandering should be taken out of the hands of the legislature, but I suppose we're also generally quite happy with our unelected judges, police chiefs and provincial/municipal officials, so I don't know, maybe we'll just disagree on that one.