Yes! Always ride with the direction of the traffic

This is my #1 gripe with cyclists in NYC, lots ride against the traffic, very annoying and dangerous.
That's a good looking bike and should make an excellent commuter. It looks from the image that has braze-ons for rear rack. Use them. It's really more comfortable not to carry a backpack.
If I may, I'd recommend Topeak Supertourist DX rear rack. I have it on two of my bikes. It works well with disc brakes, although it looks like the Dew Plus has the rear brake mounted on the chainstay so rack shouldn't be a problem. But it's a great rack anyway, has a second, lower rail for panniers so they won't interfere with anything you may have loaded on the top platform and it keeps panniers securely away from the wheel.
You seem to be going in the right direction to become a bike commuter

Please keep us posted on your progress. We're always curious to see how new commuters are doing and always ready to help, even if that means a long boring rant
Cheers!
Adam