Again, for more details about how all of these three New York State stamp issues were used, I invite readers to Michael Mahler's series of articles on the American Revenue Association's website. The specific article about the Tax on Investment stamps may be found here.
TAX EXEMPT FOR TWO YEARS
JUN/12/1918
Boxed 50-cent Battleship Stamp Cancel:
C.C.C. & ST. L. RY. Co.
JUN/1/1900
Michael Mahler scan
As Mahler notes in his definitive article, the New York Tax on Investment actually was simply a renewal of the Secured Debt tax, albeit with new increased tax rates and a new set of stamps. Because the new stamps weren't immediately available the old Secured Debt stamps were used for several months. The "carryover" usage of the Secured Debt stamps is illustrated on the C.C.C. & St. L. Railway bond shown below.
It was originally issued on November 1, 1899 and then properly taxed 50-cents with an R171 Battleship revenue. On September 18, 1917 when the owner decided to register it with the State of New York and pay the then current Tax on Investment fee of $10 for five years, a $10 Secured Debt stamp from the 1911 issue was used to pay the fee.
Cleveland, Cincinnati, Chicago, & St. Louis Railway$1,000, 4% Gold Bond Issued November 1, 1899
with $10 Secured Debt Stamp Paying Later 1917 Tax on Investment 5-Year Rate
C.C.C. & ST. L. RY. Co.
NOV/1/1899
Boxed $10 Secured Debt Stamp Cancel:
TAX EXEMPT FOR FIVE YEARS
SEP/18/1917
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