Re: The Point (Boylston/Brookline)
RE: the design & street level:
If you walk around Manhattan, the vast majority of the architecture boarders somewhere between "meh" and "fucking terrible". But on the street there is a storefront every 20 feet or less, so you rarely ever look up to appreciate the awfulness towering above. This is why Manhattan frequently beats the crap out of all other citys in the US for urbanism, its everywhere.
RE: going tall:
I am so completely ambivalent to skyscrapers I'm sure its baffling to the tall fetishists. Honestly my thought is "who cares?"
Skyscrapers can, for the most part, only be seen and fully appreciated from outside the city, or at least from a great distance from their direct area of influence.
Skyscrapers only economically make sense where the desirable area is fully built out (ie, manhattan). In Boston there is a wealth of space that has remained stagnant for decades that has the potential to be built out. Fenway is of course the poster child for this, but you could see that level of development (parking/vacant lot and single floor taxpayer redevelopment) in Allston, Roxbury, JP and Eastie for the next 30 years and still not need to go +200'.
Boston is a compact city. You can walk from most of the outer neighborhoods to the center of the city in an hour or so. In NY you can't even traverse a borough in that time.This is the main reason I think you don't see many tall buildings here, and the ones you do see have by and large been built by corporations where economics are not an issue, but image is. And if you want a paramount image, a skyscraper is the way to go.
To be clear, I'm not arguing against tall buildings. If they work, then fine. And they do work in the dense city center. What I am arguing is that Boston does not have a striking need for them. For every Kensington you could build three or more Trilogys. As has been seen in Fenway, the transformative effect of just a smattering of these buildings can holistically change the character (and economic status) of a neighborhood for the better.
So, if people (developers and tenants) want to pay the premium for a high rise for the image or views, then let them. But the net effect of several 15-30 story buildings is a far greater net positive than a single tower. This isn't the 70s where every city was clamoring for a supertall to put it on the map to help fend off white flight. City's in general are in the midst of a renascence, and it is the metropolitan aspect of living that is driving this, not the image of an iconic tower.
RE: street level interaction and towers being mutually exclusive.
The taller you go, the more "stuff" you need. A short building may only need a garage door for some trash bins while a tall one needs an entire room for a compactor or incinerator, and an office for the staff to operate it. You start needing fire command centers, more elevators banks and their associated lobbys, ventilation shafts, loading docks, BRA mandated drop off zones, redundant stairwells, communications closets, generator rooms, and parking.
Now while some of this stuff can be moved to the roof and sub levels, when it comes down to it the taller you go the more bloat starts accumulating on the first few floors. So while yes, a tall building can have excellent street level interaction, it can logistically never be as good as a shorter one, all else being equal (well, unless you took Chicagos approach and built multi-level streets to separate "ugly" things off the street, but I don't see that happening here).