It depends.
There are 2 licensing bodies in Canada - Industry Canada, which covers the technical aspects, and the CRTC, which covers programming.
It's relatively straight forward to get an Industry Canada license, as long as there are empty frequencies and you use a certified (for whatever its use is) transmitter.
It's difficult to get a CRTC license, as they not only have Canadian content rules, and look at other programming already provided in your proposed coverage area, but they also look at your financial viability. The latter is done as spectrum, particularly in urban areas, is at a premium and rather scarce.
BETS-1 is the Industry Canada set of rules for unlicensed broadcasting, and there is a specific CRTC license exemption for such transmissions. BETS-1 allows a field strength of 100uv/m at a distance of 30 meters from your antenna for FM, and 250uv/m for AM.
Anything above BETS-1 levels for broadcasting is lumped into one class from the Industry Canada perspective.
There is a special class of NON broadcast license in Canada, called RSS-123, which covers transmitting within specific boundaries, usually within arenas, or large public areas. You do not require a CRTC license for that, as it is not considered broadcasting, per say (transmitting to members of the general public). With RSS-123, you can use up to 1 watt, as long as your field strength at the specified building or area boundaries is less than or equal to 100uv/m (for FM).
There are various CRTC exemptions for other types of broadcasting, such as tourist information systems, traffic information, etc. Generally, you can't broadcast music with these uses, and your power is restricted.
Finally, you do require a CRTC license for 1 watt transmitters (anything above BETS-1 levels, in fact) if you are doing general broadcasting. You also require that CRTC license, but generally it is much easier to get one in rural and/or areas under served by existing broadcasters. In fact, there are specific initiatives to speed up the awarding of CRTC licenses in certain rural areas.
I hope that gives you some idea of what goes on in Canada. We are allowed more unlicensed FM field strength but we don't have the equivalent of Part15.219 for broadcasting, so our AM field strength allowed is less. The U.S. does not have the equivalent of RSS-123. And it is easier to get licensed with low power in rural areas. On the other hand, we have to deal not only with Industry Canada, but also the CRTC.
and that CRTC licensing body is why your airwaves are not as screwed up as ours and why you guys have much less of a pirate problem than the usa.
deregulation has screwed up our broadcasting airwaves here where you hear the same top 40 stuff on several full power stations and translators in a single market with no real serving the public aspect to it.
hell now they are eliminating the main studio requirement!!!
stations will no longer be required to have a studio presence in their community beyond the RF signal.
this is why we have such a huge pirate problem here in the USA.
i wish we had the setup here that you all have in canada.
our friends to the north are more progressive than the usa in everything from healthcare to broadcasting to social policy.