When people say whatever it takes to save VIc High, I don't believe that to be the case IMO. Sure its cool to look at but i only drive by it a handful times a year... So is it worth saving it to me? Simple answer is no, but for others that opinion might differ depending on where u live and if it played a part in your upbringing among other factors.
Selling off land does't sound like a good idea to me overall, however with Lansdowne school I would probably agree some should go. Lansdowne school used to be an airport if i recall correctly and i think its just remained since then.
Selling land in order to fund a project will lead to a similar problem down the line, its only a temporary fix. What if the population demographic shifts to a younger population in the future. Then we will have the issue of not enough land to give children adequate outdoor time that is essential. Then when the building comes to need a new major reno there wont be any excess land to sell off to fund the project.
Also many schools such as uplands where I live by are housing significant international programs. These are huge income producers as they usually pay in the 3-5 times the tuition range compared to what is subsidized per student in the province.
There are heritage structures that are totally worth saving at almost any cost. But i have to say these are more in the ballpark of the parliament and the empress.