For summer, yes! Especially weekends. For Pride Weekend, absolutely and immediately. For shoulder season and winter you have more flexibility, though the best-value boutique hotel rooms still fill up. 2-4 weeks out is usually fine outside of peak season.

Yes. It's one of the safest major cities in North America. But as with anywhere you go, be aware of your surroundings. Standard urban awareness applies.

3-5 nights covers the highlights. 5-7 nights lets you explore properly, including a day trip to Niagara Falls (90 minutes, worth every minute of the drive). 10 days and you start feeling like a local, which after 46 years here I can confirm is a good feeling.

Relative to comparable North American cities it's reasonable. Mid-range hotels in central neighbourhoods run $180–$250/night. Budget options exist from $110. Luxury starts around $300 and climbs from there. Shoulder season (May and October) is where the value is.

King West. It's central, atmospheric, walkable, and gives you an honest sense of what this city has become. The CN Tower area works if you're prioritizing convenience over character.

Toronto has strict short-term rental rules (I know, I use to be one a landlord), hosts must register with the city and can only rent their primary residence. In practice this limits supply significantly. You'll find fewer options, higher prices relative to hotels, and more uncertainty than you'd expect for a city this size. For most visitors, a hotel booked through a major platform gives you better price certainty and real consumer protection. The hotel options in Toronto's core neighbourhoods are good enough that Airbnb rarely wins on value here anyway.