Elections New England needs to draw ridings that A) Do not break up towns B) Need to be around 90k population
The City of Stamford has 130k Residents so it will be +40k, while the neighbouring town of Greenwich, which borders the United States and only borders Stamford, has a population of 60, so -30k.
Or they might release a map where Greenwich is combined with a town that it doesn't border, either going through the water or the United States.
I really love this thread, I really like New England and happily jump at any chance to have it as an independent nation in a TL. And this one is so hugely detailed and well executed, it's fantastic to read
On the issue of balanced ridings vs preventing gerrymandering, I think you'd be fine overall with just a slight change in wording. As long as the restriction was to 'not break up an existing
community' rather than using a word that also gets used for administrative divisions, then you have sufficient wiggle room to still produce balanced ridings without leaving people feeling like they've been carved out of their own town. Assuming that you're using the same divisions that appear on OTL maps of Connecticut, then if I use some English terms instead of OTL Connecticut usage it might be clearer what I'm saying.
So the big blocky rectangle currently labelled "City of Stamford" could be seen as a Metropolitan Borough, which in the UK describes what the OTL City of Stamford looks like to an outsider - an urban core that's a 'proper' town or city and a load of satellite villages and semi-rural areas, which are economically linked to the town but have their own separate community feel to them. E.g. the Metropolitan Borough of Barnsley in Yorkshire, Barnsley itself has about 90,000 residents while the borough has about 225,000, and places like Elsecar that are part of the borough but not the town feel obviously distinct from the town, even to a visitor. This seems like a decent fit in New England where, like England, there are many villiages that have existed for centuries but are being slowly swallowed up into a metropolitan sprawl spreading out from the bigger cities. So they retain a sense of identity that a greenfield suburb would never have had.
So if the OTL "City of Stamford" were considered like this, then a restriction to not break up a 'community' when drawing riding boundaries would be much less of a problem. Even if you only split off the bits north of CT-15, that's about 15,000 people moved into a putative Greenwich & North Stamford riding. It wouldn't rebalance entirely, but would help. I freely admit I've never been there and there might be folk who swear blind that they are definitely still in Stamford proper, but it's surely far less devisive than, say, running a riding boundary up the Mill River.
Finally, just to play Devil's Advocate, the restriction on not splitting communities actually works against using the 'town' border as the riding border in densely populated areas like this - were it not for signage I don't see any way you'd know you'd passed from OTL Stamford to Greenwich if you were just walking down the road. Given the relative sizes and distances, people living just west of that line near the coast probably see more of Stamford than Greenwich so any lawyer worth his salt could spin hours of argument against regarding the municipal border as a split between two actual communities.
So just my twopenneth, but as with so much officialese in the UK at least, switching from a word with a legal definition to one that's basically sui generis can make both sides think they've won the debate while still giving enough flexibility to both prevent gerrymandering and also prevent disproportionate riding sizes, depending on how you phrase the arguments around the wording