Question: How Do I Map My Property?

Jason Endres is trying to survey his property.

I recently purchased 50 acres of rolling forest land and I am trying to find the best means to create a fairly precise topographic map of the area. In addition to the physical terrain, I would like to map out property boundaries, streams, tree stands, old logging roads and stone walls. I assume I will need to buy a handheld GPS unit, but I wonder what features I will need, how much accuracy I can expect, and what software will streamline this project. I’m a complete newbie (and a confused one at that) when it comes to GPS and from what I’ve read, I’m very limited by my Mac.
Will I be able to simply walk around the property with the handheld unit and come back with all the info I need to connect the dots?