Interesting thread. It's important to have a little history tossed into the mix here, for a few reasons. First, I find it fascinating, and I'm sure others not only agree, but have done a bit of research themselves. Second, I'm currently camped in Homer, on a ledge overlooking Cook Inlet, and have been wandering AK, and the Yukon for the last month. Last, shipping in the great white north had a long and storied history.
By the time the first gold rushes were hitting their stride, the steamboat trade was plying any navigable water with a miner upstream, and making quite a living at it. At the peak, there were over 250 ships serving the Yukon river system alone. By the 1950s, roads put a stop to that. Expediting go it's start on dog sleds, small river boats, mules and even on foot, before moving up to things like model T's and "Cat trains" which were small Caterpillar bulldozers pulling a train of sleds over winter trails. By the twenties, air traffic became a player, and really hard core pilots were delivering supplies, and mail, in open cockpit aircraft. The extension of the road system to really remote areas meant that a lot of freight could be driven right to the door of truly remote gold, silver, mineral and oil exploration sites. Key remote villages can be serviced year round, with some pretty big aircraft for passengers and cargo, which can then be shuttled to the middle of nowhere in a few hours. I spent an evening around the campfire with an Air North pilot who flies Boeing 737s to gravel runways in some amazingly wild parts of northern Canada. He flies everything from Bulldozers to beer to remote mining operations. Big time expediting happens in a lot of ways, from Greyhound buses that travel regular routes in the north, while pulling large cargo trailers wherever they go, to the newest FedEx rigs for the bush. These are Single cab 4WD superduty Fords with very heavy duty cargo boxes replacing the pickup bed. There are still countless small flying services that do scheduled, or charter work to anywhere a standard plane, tundra tire plane, ski plane or float plane can get to, which is pretty much anywhere. And there are the giants in the field like Lynden and Carlile who can get anything, anywhere in the north, from a small shipment, to oil field structures, and other super loads.
Is it possible to make a go at expediting in the north? I'm sure it is. But, there are others that have a 50+ year jump start on anybody starting out, and it's an extraordinarily tough, and expensive, environment to operate in. Personally, I would do it for one of the proven companies and put a full year in behind the wheel of somebody else's truck, before I spent a minute learning the hard way on my dime.