Hi Eduardo
Some of your questions would be easier to answer if you gave us an idea of your income, maximum amount that you can spend on a home, and whether you prefer the suburban environment to downtown living. You may be hard pressed (for instance) to find something suitable for a young family within a reasonable commuting distance to downtown Toronto for 285K. The Greater Toronto Area (City of Toronto and surrounding communities aka GTA) is a very expensive place to live. You can get a good sense of housing costs by browsing through
REALTOR.ca - Welcome (formerly MLS) site.
-Desirable areas include those closest to subway lines and located near certain schools. Unlike some US cities, many people have chosen to live close to downtown, and thus make Toronto's core a desirable place to live. To generalize, areas to avoid are Toronto's "inner suburbs", which are located in a ring around the core near highway 401. It's hard to advise you not knowing your preferences.
-Thousands of people commute to work in downtown Toronto from outside communities such as Burlington, Oakville, Mississauga, Hamilton, Barrie, Whitby, Pickering, Oshawa etc by commuter train (the GoTrain). Most of these commutes by train range from 30 to 60 minutes. Others choose to suffer in their cars in some of the worst gridlock in North America. Commuter hell is why some choose to pay a premium to live closer to downtown. I think it's possible to easily spend 2 hours in your car one way.
-Toronto is Canada's largest city, it has all the attractions of a large multicultural city : professional theatre and performance, music, art, food and cultural festivals, concerts for every taste, restaurants of every type and price point, art galleries, parks, professional and amateur sport, etc. Some nice Toronto attributes : walkable charming neighbourhoods, Toronto Islands park. Some not so nice : bland ugly architecture, hard to quickly escape to countryside (located in sprawl) and sometimes lacks a certain "joie de vivre" (just my opinion).
-As Canada's largest city, Toronto is the hub of Canada's finance and insurance industries, therefore our major banks and brokerage houses are headquartered here. Most major tech companies (Microsoft, IBM etc) have offices in the GTA - Toronto also has quite a few startups. Toronto is where the majority of Canada's media outlets are located and has a large film, TV and video game industry presence as well. There are also major research hospitals located here, as well as three universities. This is off the top of my head, I'm sure I'm missing something obvious.
-Average winter temp is probably -5 to -10 celsius. We do not get as much snow as cities like Buffalo or even NYC. The cold in Toronto is damp however and it often feels colder than it actually is.
-Crime : Toronto is an overwhelmingly safe city. Gun crime is rare and mostly confined to gang-related activity. To generalize, gangs tend to be located in "inner suburb" areas.
-Schools : don't know this one. You can google this though, there is a lot of information on which schools are better performers in Toronto.
-Taxes : Property taxes will differ whether you choose to live in the City of Toronto proper, or in another surrounding community. City of Toronto taxes are based on the assessed value of the property. Check out this link from the City.
City of Toronto: Property Tax
Hope that helps.