It is not a simple issue.... Ham (or amateur) radio licenses should not be confused with Industry Canada licenses. As mentioned previously it is unlawful to transmit without a license and this refers to an Industry Canada radio license that specifies the frequency that is allowed to be used in a specific geographic location. I believe that Industry Canada has been working on a more simple solution to the logging road issues but this needs to be confirmed with them. You are responsible to have the license that specifies the channels (or frequencies) that are programmed into the radio. There are ways to do what you want that are not quite legal (in Industry Canada's eyes) and that would be to purchase a user programmable (or editable) radio, obviously this does not meet IC's guidelines as you may not have the frequencies you choose to program listed on your license! Motorola make a handheld model called the HT1550 that allows this and can be charged with a car charger (expect to pay $1200 for this radio) or TAD make a mobile called the M10 that can (when modified slightly) be programmable, the TAD has to be hard mounted in the vehicle with Antenna etc., I am sure there are lots more radios that can do this but I am not going to get into that :-) these are just the good ones.
I recommend you do the following:
Find out the area you want to use the radios and the frequencies you need, then ask the company operating in the area(s) for a letter of permission to use their frequency(ies). Next buy a mobile or handheld VHF radio and submit an application to Industry Canada (with permission letters) to get your license, this does cost $41 per year, then get the radio programmed and you are away :-) you can have many channels on a handheld radio for different areas and you don't pay extra for it but you must have the frequencies on your license or risk having your radio confiscated plus a fine or warning if caught operating outside the IC rules (sounds like fishing doesn't it).
Most importantly talk to Industry Canada in Surrey, they will help you with the rules. Be careful with radio dealers that are willing to program frequencies into radios without permission letters, they open themselves and you up to the wrath of Industry Canada.
Radio frequency is managed for many obvious reasons such as public safety for example so be carefull what you purchase and where you get it from.
No I don't work for Industry Canada but I do work for a radio dealer so I have talked with many people about this.
Regards,
Tinhat