'Jump right in' they say! 'You never know where that big leap will take you!'
I am a firm believer in delving right in, however, leaping blindly is not the best idea, some type of assessment must be taken into consideration.
I have fallen into the trap of doing something for free. As we all know, the 'free' in freelance is a misnomer, AND this is where people get duped.
That being said, creating a list of project pros and cons is a great way to start. I prefer a compiled list of whether I should do it or not. It can be a written list or just a mental note. Also, using your instincts is still a good old fashion way of assessing a 'leap', if something doesn't feel right or is too good to be genuine, just don't do it until you are sure of the possible outcome. We can't foresee the future, but we can prevent giving away the worth of our talents for nothing.
By the way, if communication isn't your greatest attribute, find a creative advocate who can speak for you.