Has anyone built both the Chesapeake and the Shearwater and how would you compare the build time and complexity of the two?

We've built a handful of Shearwaters and scores of Chesapeakes. I think the elapsed building time of the two boats is about the same. We kept an eye on the hours when we built the second Shearwater 17 and it was about 80 hours total. That was moving fast, and often with two people working on it at once.

There are no scarfs to glue and no sheerclamps to plane on the standard Shearwater, and that reduces time compared to the Chesapeake. You gain all of that back in putting the Shearwater's deck on. Actually, you have the deck on and off about four times in the process of assembling it. None of the processes are any more difficult than the Chesapeake, just different.