Best Way To Manhattan Bridge - WHOOPS
Whoops. Please make a right from Plaza Street on to Vanderbilt. I am sorry, I was writing way too quickly at work. Thanks for catching that mistake.
Also, don't worry about "the hill" in Prospect Park. As a new rider, it will be hard the first few times, but as you adjust and know how to use your gears it will get pretty easy. As hills go, it isn't much of a hill. One piece of advice, as a new rider, make sure you use an easier gear on the hill or the bridge. Avoid getting too much of lactic acid burn in your legs. If you get too much of a burn it can wipe you out. On the other hand even if you increase your cardio and are huffing and puffing it will not make a big difference because once you level out, you recover very quickly.
Finally, you have a great idea in trying the route and then variations on the route on weekends. This way you can experiment, get use to the geography and have some fun all at the same time.