Long Story, but back in 2010-ish I acquired several items that belonged to ice yacht builder George Buckhout.
First I bought copy of the Club Book of 1890 on Ebay, which was Buckhout's personal copy. The seller was from Poughkeepsie. He tracked me down later saying he had the toolbox, which he planned to part out. I bought the box & tools and half of the planers.
Here's a short write up about the tool box I did for an expo at the FDR historic site a few years back
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How it looked when it was first opened.
Check out the long bronze stanchion in the bottom on the left. Here's an ad for them from 1930:
 
Drafting weights ("dolphins"?) I had to search about these:
"They’re called drafting weights, lofting ducks, spline weights and other names. They are used to bend damp wood strips and pieces. The pointed tips hold the wood in place, while the weights prevent any movement as the wood dries. In this way, wood can be molded permanently into curved, bent, or even spiraled shapes." The rusty piece, upper right, is a mold for making these.  
A torn letter was in a box with references to an iceboat he was building.
Also, a sketch for a runner plank.
 The toolbox on display at the Wallace Center in Hyde Park, the FDR home & library, when FDR's Hawk was on display.
Buckhout's planes had been removed and I was only able to get 6 or so
from the collection, to go with the chest. The seller wanted to keep the others.
Here are some of them:
   
George Buckhout's Obit - June 15, 1948:
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