Tom,
I think I've settled on the Garmin Touring GPS. I've heard some negatives about the Touring but with it being my first attempt at this technology I'll go with the less expensive model for now.
Have not decided on which program to use yet. It will likely be RWGPS as I just joined it to see what they had to offer on the free service. I don't quite understand a lot of the terminologies yet so I can't really say if the paid program is for me or not.