Hamilton is truly awesome. has everything that Toronto has but with fewer repeats of the same thing and no lineups. The library system is fantastic. Farmer's market is actually useful - you can shop there, not blow your wallet to bits, and come home with real groceries, not just artsy-curios and specialty mustards. You can live an urban life and when you need the convenience of suburbia it’s right there, 15 minutes up the road. Hamilton is also well-placed to enjoy Buffalo, south-western Ontario, and Toronto. It is the perfect location. It's got the university and Copps so lots of entertainment and shows and sports. From 1998-2009, Hamilton was Ontario’s best-kept secret.
But it is not 2009 anymore. There are downsides.
As a former Hamiltonian (now living in Toronto), this is the most accurate pro/con list I've seen, minus the pollution which is vastly overstated based on stereotypes.
To some extent, an emerging problem is that the prices aren't that great of a deal anymore (particularly if you add in the commuting costs of Go Train plus TTC), unless you're willing to live away from the GO Train or in a neighbourhood that is sketchy. And when I mean sketchy, I don't mean Toronto sketchy. I mean hookers on your driveway sketchy. I mean sleeping stranger in your backyard sketchy. I mean don't go into that laundromat after 8 PM sketchy. I mean schools you're not sure you want your kids to go to sketchy.
But the real problem in the Hammer is jobs. There are fewer of them. There is less variety. If you find one, it is usually not as well-paying as it would be in Toronto and it's likely one of the only available jobs in your field, which means you're one job-loss away from financial insolvency.
Another downside is its suburbanism. Yes, downtown Hamilton is relatively dense and its attracting lots of independent shops and stores and it feels like you're living in The Junction. But imagine The Junction, stretched out over double the land mass, surrounded by suburbs and divided up by big, four lane streets, with no streetcar, no subway, and limited bussing.
People see the cutsey shops on Locke, or the north end or even Ottawa St and envision family walks to shops and a pedestrian life with a paper bag of groceries in their arms but that's not the case. The things that make Hamilton a bit edgy aren't useful - you generally don't shop at the Caribbean mini mart, don't eat frequently at the Portuguese Association, don't spend evenings at the Navy Hall and only need a few things from the bakery, coffee shop or store that sells organic honey and candles.
You need a car and you need if for everything. The places you need to visit week in, week out are a drive-away, often out in a suburban power centre. The places you want to eat at are spread out across the city. You're not a walk away from a hardware store. If you're going to do any decent amount of shopping at Jackson Square or the Farmer's Market, you're not going to be able to do it via the HSR. I mean, look where the hippy-dippy food co-op located - a place where the parking lot is bigger than the store, right on York Boulevard, walkable for the residents of about three streets and that's it.
If you're self-employed or can work from home and you'd don't mind a suburban lifestyle, or you feel really secure in a job that's in Hamilton, take the leap to Hamilton and you'll never ever ever regret it. I miss it all the time, we go back at least once a month.
If you don't want to use your car all the time for everything, or you need to come in to Toronto more than twice a week, don't bother.