299 - presumably the financials did not assume increased local population? Extending the short turn to Glencairn's turnback track might work if there was the additional customers to back it up, perhaps with a mandatory purchase of metropasses by developers to pass on to owners as part of the deal. There would also be the benefit of providing custom for a full-time 15 and could be fully market value properties.
Ideally, the decking could cover some if not all of the airspace from Viewmount south to Ridelle to connect Viewmount Park to the smaller park on the other side and counterbalance the density increase.
Between Lawrence West and Yorkdale further housing could be constructed as a market/TCHC mix as at Regent Park, which could then be initially used to house relocated residents from buildings being refurbished or demolished rather than displace them all over Toronto into whatever spare rooms TCHC has in the 416. A similar "park connection" could be done between Flemingdon Park and the small park on the west side of the Allen across from it.