To the guy asking about wx: If you just want to get a feel of what's expected, you're not a wuss.
If it's legal, or forecast to be legal, you should be able to make the flight. I never went off schedule when I was flying checks, but like one of the guys above me, I did wind up sitting on the ramp to discover the banks weren't going to move their freight.
With that said, telling someone "Ice, thunder, fog and flames, I always made it happen on time!" isn't any great demonstration of piloting ability. In fact, I'd say I'm just average as pilots go. See, it's not really that tough to keep your needles centered. Ride a dot high to avoid dirt and towers, and you'll still make it in. It's not really that tough to fly a big recip in cold weather; just don't jerk throttles around or lug the engine. What IS tough is staying awake. I'd wind up babbling like an idiot with ATC just to avoid falling asleep, and even that would only barely prevent me from turning into a cockpit-zombie. What IS tough is dealing with a failed janitrol heater at 2am on a frigid, foggy, January night. Even three layers of socks won't keep your feet warm for long, and you can't think very well when it's -20 in the cockpit. Starting engines, and keeping 'em warm when your driver runs late isn't easy either. As you spend time flying your freight, you'll learn how to employ various tactics to deal with weather, like the rest of us. Read some books, and try not to stress.
Reading brings another thought to my mind. You can deal with a lot more when you study the geography within 1 hour of your base and along your route. Rather than staring at a hand-held GPS, know VOR frequencies, terrain, locations of 24hr FBOs, NDB and powerful AM radio stations, what airports have ILS and their localizer frequencies, etc. You'll have more mental energy to focus on dealing with whatever situations are on your plate for the night. I still stare at old charts, plates, sectionals when I take a sh-t, and that studying still pays off.
Good luck, and stay safe.