Thanks Carely, glad I could help! That picture was actually take on a five day tour across South Korea. However, I use that same configuration for commuting. My day bag goes in the rear and stuff I need access to during the ride, like an extra sweater or hat, go in the front basket. If I buy a lot of stuff at the store then I just wear my day bag to free up space in the saddle bag. Works great. I love rear baskets though too. The saddle bag just works a little better for the touring that I do.
If the larger Wald basket, which is what I would recommend for you, does not fit underneath your existing saddlebag that carries your essential, consider adding a small and light handlebar bag. You could even make a good one out of an old fanny pack.
Make sure to post some follow up pictures for us after you get the rig all set up!