Here's a contrarian view.
First of all, expediting isn't rocket science. You both are already making deliverys and pickups so you know how to do that. You can learn about good and bad areas, deadheading, rates and HOS by reading this website. Your biggest challange (my opinion) will be living on the road with each other. This will either work or it won't. I don't think tests or practice will have any baring on it.
Neither of you have any heavy financial comitments, so this might not be a bad time to buy a truck. You don't need all the bells and whistles to start with. If you shop carefully, you can get a decent truck for $20,000. If pairing up doesn't work, one guy can drive and buy the other out or you can lease it to someone. If you own, or are buying, the truck it will only have two mouths, not three, to feed. If your goal is to own trucks, why not just get on with it. I do agree that spring is the optimum time to start.
Get familiar with
https://www.fmcsa.dot.gov/. Learn the rules and regulations and what it takes to get your own authority. With the ability to broker your own loads, you can sign on with several carriers and brokers, and find your own customers, once again sidestepping middlemen. This is the way I started but I wouldn't reccommend it for a single. With two of you, one can mind the computer and phone while the other sleeps. Another good website is
Owner Operator Independent Drivers Association, Trucking Association
Many come on here, full of ambition and the desire to be the greatest expediter of all time, but most seem to disapear pretty quickly. Expediting ain't Hollywood. There is no glamor and the money diminishes while expenses keep rising. You may do OK sitting in a parking lot waiting for the qualcom to go off, but to do well, you need to be proactive, make some contacts and seek out business.