I am facing the same problem that the OP has with a Cuban family friend of mine , they can not afford to subscribe to pay services and the also have a single CRT TV. So Anthony you are telling me advice them to watch Analog Canadian Stations from CN Tower only with an indoor antenna?.
Lets assume there is no multipath at all, lets assume there is clean LOS , and lets assume the analog reception is 100% then they would get all 8 major Canadian Networks in the area (including E! from Hamilton) , all in analog. Fine , no problem , you get a picture and sound untill 2 years from now that you will loose everything. Only investment a cheap indoor antenna. Total 20 cad only probably.
There is a problem; big problem, that scenario in real life does not exist for most people although the OP says he/she has a perfect "view" of the CN tower so that could be different.
The reality for most people is that you need an outdoor antenna not necessarilly located outdoor , could be in the Attic. And that one will cost you from 30 to 50 cad for a good antenna that covers up to 45 miles. That one will also get you good 100% reception of Analog.
But there is a problem now, you already spent 30 to 50 cad and now have an outdoor antenna that could potentially give you extra digital channels from Buffalo. Yes, those extra channels have different programming and for some people like me better, like PBS, Universal Sports and RTN Subchannels. Guess what? by going digital and the converter box route you also get, at least, the EPG embedded in the PSIP info that the US broadcasters transmit. A service that analog does not have (it does but requires the tv to have the TV guide feature).
So in other words I am advicing the OP to invest 100 cad total , half in the antenna half in the conv box rather than just 20 on an indoor and hope for the best on analog or 50 cad and be happy with analog canadian stations that most of the time just repeat US content.
but at the end of the day , life is about choices right? , so we give as much info to the OP and it is him/her to decide what is best.