I have a $20 Conair clipper set from Wal-Mart--- it came with all the attachments, even a DVD for learning how to use it--- but after using it for about 10 haircuts, the blade is too dull to do a decent job anymore. Now I just use my beard trimmer, which is a $40 set by Wahl (also from Wal-Mart, the poor man's mecca). The Wahl trimmer seems to stay sharp far longer, just doesn't have the longer attachments like the Conair (the longest you can leave your hair is 3/8 of an inch). However, I've heard Wahl is a pretty good company in general; you might look for one of their hair clippers. I'd steer clear of Conair, though, unless you have the money to spring for a professional quality clipper set.
As per how easy it is, I always keep my hair much shorter on the sides and back than on top, and that can be tricky. If you plan to cut it all the same length, it's easy, but as Cindy mentioned, you can end up accentuating your feminine features by shaving/buzzing your hair. My recommendation is make sure to leave it longer on top than on sides and back, and have someone touch it up for you when you're done, to make sure everything is even.
I've been cutting my own hair for about 3 years now, and no one's ever told me it looks bad... that must account for something, right?