From my understanding, that lot is part of the Salvation Army Toronto Grace Health Centre, which complicates the development options for it.
To me, this site is a very unusual one for the reason above.
Rather than going condo; I'd like to see a very vertical long-term care home on the lower levels (retail at ground); make it C-shaped, with a courtyard in the interior, integrate Toronto Grace (palliative care); but make space for a single, slender, hotel, because there could be cost-sharing advantages for kitchen facilities which form a market-pay off for the long-term care.
7 storeys at the back, 14 along Church, climbing to 21 at Bloor, but 28 for a tower.
The City desperately needs more long-term care beds, what a great spot for 350 of them.