Generally, it is unusual to tweak a subway route so much in order to hit any particular condo cluster. Sure, this is better for the Liberty Village residents, but worse for those who lives or will live at Queen West or Dundas West. Even if the density there is not as high as at Liberty Village today, highrises will surely go up there in the not-so-distant future as the downtown areas continue to gain residents.
And then the Queen West / Dundas West residents will have to deal with the same Ossington or Dufferin buses in order to get to either subway line, OL or Bloor.
Not sure about the Kitchener Line capacity, as it will be consumed by GO trips from the outer 416, as well as from Brampton / Kitchener etc. But even if Kitchener line can do the job of relieving Bloor West subway, and thus OL doesn't need to go back to Bloor in the west - I would still think that the OL route straight along Queen West to Roncesvalles would be a better choice. More coverage overall, and shorter average bus trips if the whole area is taken into account, not just Liberty Village.
Of course it is too late to change the OL route now. However, we should be aware of its drawbacks, as they might cause new transit bottlenecks that will have to be addressed.