The handstamps on the 10 and 4 cent stamps differ. See the last letters in the name Quackenbush. These stamps were likely used on equity transactions of some kind.
Edward Quackenbush would become a successful financier and community leader in Portland, but in his youth he lived an exciting and varied life. He was a pitcher at 27 for the Portland Pioneer Baseball Club. Before then he arrived in Portland as a well-educated New Yorker, who studied political history, composition, philosophy, English, and advanced math before dropping out of school at 15. He moved to Iowa and campaigned for Lincoln, tried to enlist in the Union army at 21 but was denied due to a heart condition, then settled out west, working at various times as a cowboy, cashier, and bookkeeper. He arrived in Portland in 1865, got a job as a bookkeeper, worked in the hardwood lumber business, became president of the Y.M.C.A., and helped establish Portland’s first telephone company, the Pacific Telephone and Telegraph Company.
Many railroads used printed cancels on the 1 cent battleship documentary for their use on waybills. Far fewer used them on the 2 cent documentary. The International & Great Northern Railroad was a railroad that primarily operated in the U.S. state of Texas. The I&GN, like other railroads of its time, had many financial troubles and went into receivership on several occasions. Jay Gould acquired control of the I&GN in December, 1880, but was forced to sell it in the early 1920s. Finally, on March 1, 1956, the I&GN was bought by the Missouri Pacific Railroad Company and became a major part of its network.
From the book "The Story of the Trust Companies, by Edward Ten Broeck Perine:
The United States Mortgage Company, established in 1871, first undertook a trust and deposit business in January 1893. Among the names of the incorporators are found those of J. Pierpoint Morgan, Abiel A. Low, Charles G. Landon, David Dows, and other men who were large factors in the financial and business life of the city, state, and nation. In common with the Guaranty Trust Company, its expansion was promoted by Mutual Life interests. After two years of operations under the old title its name was altered in 1895 to United States Mortgage and Trust Company. The "Mortgage Company" as it has been familiarly known, has continued to carry a large line of conservative real-estate loans, place mostly in the larger cities of the West and South.
The 1898 series of US revenue stamps entered use on July 1, 1898 after passage of the tax act a few weeks earlier. But a major cause of the war, the destruction of the Battleship Maine, happened months earlier on February 15, setting in motion a growing war cry across the United States.
Wreck of the Battleship Maine
On February 15, 1898, the key event that set in motion the Spanish American war took place in Havana Harbour. The sudden explosion of the Maine killed 260 American sailors and officers and sank the battleship. The destruction of the Maine created an uproar in America, which, influenced by newspaper publicher William Randolph Hearst, immediately held Spain responsible. Hearst's New York Journal published a story with the headline, "The Warship Maine Was Split In Two By An Enemy's Secret Infernal Machine!''
Albert Loeb and Company was a banking firm located in New York. Albert Loeb died about two years after the cancellation of this stamp at 42 years; the New York Times reported the cause of death as apoplexy.
Logan & Bryan was famous as a "private wire" brokerage house. With major offices in both New York and Chicago, the brokerage maintained its own private telegraph line between the two cities to enable it to conduct its business. While I am no expert in this era of economic history, I would expect that the information and service advantages from such a line were enormous, permitting at a minimum fast customer service but also creating incredible arbitrage opportunities.