What is unreasonable about 38 storeys? I think it's fine.
I would love to see more development in this hideous wasteland between Spadina and St. George.
That's quite the hyperbole. Bloor between St. George and Spadina is arguably less engaging than the more commercial area west of Spadina, but it's nonetheless lined with generally well-maintained buildings and interesting landmarks: the Jackman Humanities Building, Bata Shoe Museum, the respectable PoMo Holiday Inn, the Bloor Street United Church, and the U of T's high school. It's not even unattractive, let alone hideous. The public realm is in good shape and clean with buried overhead wires, though the large expanses of concrete sidewalks and asphalt roadway are generic.
Considering that this tower will likely be built on the parking lot behind the church, I don't think that 38 storeys is anywhere close to what could be considered appropriate. It doesn't even front Bloor but rather a side street, where its neighbours consist of low-rise housing and some relatively low towers. On Bloor, that kind of height could be more reasonable, but it's still in excess of the present built form.
There's also an attractive vista of the Bloor Street United Church's picturesque spire with four turrets peaking over the trees and buildings on Huron Street, which is visible as far south as Wilcocks Street at New College. At Huron and Wilcocks, you can see the University College tower and spire to the east and the church's spire to the north. This vista cannot be defended like the more prominent vistas in Toronto such as Queen's Park since it was not likely achieved through deliberate urban planning and not that of such a critical building, but still something positive to note in the present built form of this part of the city. Through the use of setbacks, a tower development at this site can preserve the traditional vista of the delicate spire against open sky and not overpower it.
Lastly, one can't ignore the ridiculous name of this project, which seems to suggest that there's something wrong with it. It is located in one of the more interesting neighbourhoods not just in Toronto but on this continent (and perhaps beyond), and it is the neighbourhood where Jane Jacobs chose to live. This name is vapid colonialism at its worst: rather than embracing and promoting the fascinating and highly-relevant local context, it substitutes an image from from a world-dominating place that's utterly irrelevant. I'd say it's even offensive because it seems to be dismissing something fundamental to what makes this city great: vibrant and beautiful neighbourhoods like The Annex where worlds collide in a peaceful place. This place is one that can accommodate students and struggling intellectuals, affluent professionals, leading thinkers, and people who like to go out and party, even if Bloor and Huron isn't the greatest part of the neighbourhood. In terms of this development, many changes would be needed to make it palatable.