Raise the Hammer

I'm not going to get to everything here, but I'll address a couple points. First, your urban density myths link isn't working.

Bilbao Effect - I realize some other cities have gotten it wrong in trying to emulate that, but for Bilbao itself it radically changed that city, it's economy and perception.

My family moving to the 45th floor - 5 of us would be a bit crammed in a one-bedroom unit. I'm aware of people who love that lifestyle and would be willing to pay for it. Heck, I see 1 and 2 bedroom lofts/condos in buildings like Allenby and Core Lofts selling for as much as my new 3 bed, 2 bath home in Strathcona. Once the kids have moved out? I could see us doing the condo lifestyle.

I know you and I agree wholeheartedly on planning and design guidelines.
I would shudder to see blocks of downtown Hamilton turn into what Toronto has done too much of - blank streetwall with a glass tower above. It's why I like the Portland, Vancouver and Manhattan model. The built form must come to the street, have retail/dining units, patio space and have a continuous streetwall full of business, life and amenities. Whether the buildings top out at 25 floors in Portlands Pearl District or 50+ floors in Manhattan is less important than how they look, feel and function on the street. I've seen 3 storey buildings that are disgusting at the street level and I've seen 70 storey buildings that are wonderful, inviting and human in their scale at the street. Considering our city is rather small, I think it makes sense to add some floors to our height bylaws and increase the downtown density while we can. Downtown Hamilton is very small compared with Manhattan or Vancouver. We don't have the luxury, as I said earlier, of doing the Paris model. It works great if you have dozens of square km to fill with nothing but 6 storey buildings. We have a handful of parking lot blocks along King, Main, King William, Hunter, Bay and Queen to add our most dense properties.

Let's design them well and ensure that they are buildings we can be proud of on the sidewalk patio and from the skyline lookout at the Mountain Brow.