I cannot speak for Jeff but I can relate my experience on my recently completed Pocketship.
Pocketship is certainly doable as a first time boat because I just did it. However you will be learning on the job and my filleting skills still need a lot of practice to come close to Jeff's high standards. I encountered some minor problems but nothing that I was not able to overcome. Full details are in my blog including how much I saved by building from plans instead of a kit.
http://pocketshipadventure.blogspot.com/2009_08_01_archive.htmlHowever, my savings include the exchange to Canadian dollars and the higher shipping costs to Canada. I estimate it took me 100-150 hours extra to transfer all the patterns and cut out the parts. Working from plans only you also have the fear of whether or not you cut everything out accurately and whether the boat will actually fit together.