When searching images such as these it is extremely difficult to read the clauses printed on them about the redemption terms, either due to elaborate script or fine print. Is there any historical examination (preferably academic, but any will do) of the variety of rail bonds and how their issuance and financial terms differed, especially their redemption terms?
On a similar note, did any early US oil exploration companies finance themselves by issuing bonds redeemable in barrels of oil?
Railroad bonds that were directly redeemable for miles of passenger and freight transport services is not something that I am aware of. However, there were more than one thousand railroads chartered in the United States and more than five hundred of them actually built some track. This was not something I ever saw done with the 125 largest (Class I) railroads that existed in 1907, when the Elkins Act really tightened up railroad financing, under the authority of the Interstate Commerce Commission.
There were instances of railroads that would direct their route through communities that were willing to buy their bonds or invest in their stock. These railroads would by-pass towns that did not invest in their company. An example of this was the New York & Oswego Midland Railroad of 1866. This company bypassed the large cities of Rochester and Syracuse, because those two towns would not invest in this railroad. The railroad went between Oswego NY and Jersey City NJ and was completed in 1873. It was bankrupt in 1875 and reorganized as the New York, Ontario & Western in 1879. It was able to get Rome and Utica New York to invest in bonds, in order to build branch lines to those cities. New York state allowed this practice, but New Jersey and Pennsylvania prohibited it. When the New York Ontario & Western built their 52 mile long branch from Cadosa NY to Scranton PA, it had to borrow the financing from Wall Street investment banks. The city of Scranton was not allowed to invest in this railroad.
Source: "The Historical Guide to North American Railroads" by George Drury