My baking skills are basically zero and my daughter wants to make a cake for her school's cake contest.  What is the easiest way for a newbie to re-create a Monopoly game board on a square cake?  We bought fondant and edible markers, but I am afraid we are too green to pull off the fondant...thanks in advance for any tips!

You will never know if you don't give it a try.  

Go to you tube first and watch some videos of how to apply fondant.  Also watch videos on applying the undercoating, be it buttercream or ganache.  You will only get good coverage with your fondant if your undercoat is nice and smooth