Gone are the day of free handsets, too. You should be. I should be. I feel that digital is worth the money, especially due to the features, and is not so expensive relative to analog. Go with digital if you are in a digital area.
Some phones are only available with certain networks.
I think price is the last thing you should look at after determining your time, network, network features, and region parameters. There are no network features on an analog network. On the other hand, most digital networks allow your phone to receive email and short messages, use callerID and call waiting, and set call forwarding. Omnipoint allows users to access information, such as weather, by sending a message from the phone. Omnipoint also has a voice dialing feature.