I just recently put on a cheap-a$$ film on my white iPad 2, and I'm quite proud to say that it was done perfectly.
My advice for putting on screen protectors for iPad (or any device in general) is to buy a pack of nice quality microfiber cloth. The dust cleaning cloth that comes with the films usually suck really hard.
Get under (very) bright light, and have a large surface to work on. Align the film on the screen to have an idea of the cutouts and size of the film.
First wipe the screen with the microfiber cloth to remove oil/smudges. Then with the help of the bright light's glare, identify dust and remove it with a corner of the cloth. Be extremely OCD about it until you are confident that there is no dust left on the screen.
Set the cloth and other junk far away from your work station, leaving only the device, the film and a roll of scotch tape. Start peeling the backing film away from you (so that the peeled side points towards you) and align the edge to the bottom edge of the screen, pointing towards you. Make sure you have an idea of how much room you should leave from when you first align the film. Set the bottom edge in place when you feel like it's perfectly aligned. Then with a little pressure of your fingers, set down the film while at the same time slowly peel away the rest of the backing film.
Don't worry if you see bubbles and dust under the film when you set it down completely. Remove the second backing film on top (if any). Then take a piece of scotch tape and stick it at the corner where you see dust/bubbles. Have another piece of tape ready and lift up the film from the corner a little bit with the first piece of tape. Slide the 2nd piece of tape under the film and remove the dust. Replace the film when done.
I generally don't recommend using any squeegee as they usually make things worse. Thats especially true when dealing with air bubbles. A small lift with scotch tape will usually eliminate any air bubbles.
Sorry about the wall of text - typed it with my iPad while at work
