On Wednesdays I ride my bike from Brighton to Carlton, in Melbourne. It is a beautiful ride,taking me about 45 minutes, with most of the trip along the bay trail beside the beach and on the path alongside the Port Melbourne Light Rail. This track is a very safe way to arrive in the city. I then head along the banks of the Yarra up to Swanston St, and then head up Swanston St. Riding is exhilarating and a wonderful way to start the day.
After a long afternoon session I am sometimes a bit daunted by the cold and dark, but with my reflective gear and my lights flashing I set off and soon warm up. I recently traded in my 26yo bike for a new one with disc brakes, and I just love the smooth gears, and the security of having good brakes even if it is raining. Mind you , if it looks really bleak I have been known to hop on a train with my bike! I am starting to ride on Mondays and Fridays too, but have yet to do it on Tuesdays and Thursdays, when housecalls are a possibilty.
I agree with your tips- panniers are a great investment, and add to the feeling of freedom when you are riding. Planning the route is the most important step- it has to be as safe as possible. Melbourne has a lot of bike paths and routes that may surprise you. Bicycle Victoria has some great maps and other resources - have a look at www.bv.com.au