Jake: That's how I was taught growing up as well. The sides of a vessel (larboard, etc) are of Italian origin as modified by the Admiralty. Leeboards, are of Scandanavian heritage (lœ or laa as in the ocean or wet side) as seen on shallow draft schuyt, botter, etc hull types. Apples & oranges.

Kendall: When the log is first thrown it is directly astern. As the vessel is "set" (see Jake's dictionary) to leeward during the timing run the log will appear to drift windward. The angle can then be measured with compass, pelorus, sextant or just fingers at arms length. A little trig yields leeway.