Yep, proudly from O-town. I guess I'm a Torontonian now (living here nearly 3 years now), but it's good to remember where you're from.
In terms of density in the Annex, I wouldn't advocate anything tall for the neighbourhood streets (other than those like Walmer or St. George that already have apartment towers), but along Bloor is fair game for just about any height for the stretch from Avenue right up to Spadina (possibly Walmer). West of that any development should be avenues scale.
Also, I'm not sure why there isn't more development up along Dupont near Dupont station. Personally I feel like that is an undervalued/underdeveloped node with surprisingly good street life and interesting retail/restaurants. I wouldn't be surprised to see more action there in the near future.