What an awful idea. Why not sell off the naming rights to streets, schools, parks, bus routes, etc.?
I like the adopt-a-station idea, although I'd rather see things kept as they are now. It would make more sense to raise the parking fees on municipal lots/tax businesses with parking lots per meter square. The money would go to the TTC, it would get more people to reconsider public transit, and isn't that what we're supposed to be doing?
Above all, it would make the city look ridiculously cheap. Added to the confusion, any money made through this scheme would be lost multiple times over when the tourists get frustrated and stop coming.