Welcome to the site! While things are slow right now but it also can be a good time to start as it will likely be all uphill from here.
The first thing you have to ask yourself is do you have some cash built up that you can use to float your new business along. There are start up costs, everything from getting you business registered, costs incurred equipping yourself with the right vehicle and the usual orientation and start up costs (like the lag between doing the run and then getting paid for it). I can't stress it enough, you need start up cash, not a loan.
It's key to remember you are a business. The expedite industry is VERY different from just about any other trucking deal out there. In expedite it is all about the customer and what they want whenever they want it, that's usually why they use expedite because something has caught them off guard and the shipment "has to happen". There is a lot of waiting for loads, almost nothing is scheduled or typical. There are loads you could do but others will get because they are better equipped or their type of truck needs to be moved to where the load is going etc. If you get down on it and the "man they are pickin on me" attitude pops up you will not enjoy this at all. That attitude is real easy for anyone to get, we have lots of time to think, usually aren't aware of the big picture, and, we are running a business that we only really care about our own pockets....human nature.
Being from Midland, you are away from the big freight lanes, how comfortable are you with being away from home for long times? True, you will be automatically coming back to Canada but if you drop in Mississauga and then deadhead home a lot it will cost you a lot of money. You may want to call a local courier type company and ask them if they do any long distance or US work. I started that way (with a pickup no less) and it was a great way to learn a few things and still have the security of knowing there was local work to fall back on. I'm glad I did it as it really helped me know what to look for and expect when I finally made the move to a big carrier.
Read up on here about the things newbie's have encountered, remember to keep in mind that being a Canadian makes it different about what loads you can take (ie no US to US loads) and you will be crossing the border A LOT! If you don't have one, get a FAST card (it takes a while to get it). Even if you aren't crossing the border with FAST approved freight it will help as it shows the US Customs guys you are one of the "good guys" and are squeky clean as far as criminality etc. They won't ask for it but when they punch you in and see that you are FAST approved, then all they care about is the load.
Read up (this site is a goldmine of info), it can be a very challenging business but it is also very rewarding if you keep the right mindset.
