Inconvenience caused by living at a distance from Main Street was alleviated by changes in Post Office procedures and the dispersal of retail outlets. The first collection boxes for mail were set out in 1884. Three years later rural home delivery eliminated the necessity of going to the Main Street Post Office to post or receive mail. Students and east-end residents increasingly declined to make the trip downtown and shopped on State Street or ordered by mail from Detroit. To meet their needs, Main Street merchants established branch stores on and around State Street. Combined with newer stores, the branches created a whole new business district and contributed to a growing distinction between the University community and the original town of Ann Arbor.

In spite of the city's substantial prosperity in the late nineteenth century, local businessmen were uneasy because the stability of the town's economy was dependent on The University of Michigan. As other midwestern states established colleges and began to compete more successfully for students, the probability increased that the University's enrollment could drop and with it sales receipts. In addition, while profiting from the second business district, the Main Street merchants feared its potential as a competitor. To insure a sturdier economy, everyone agreed Ann Arbor needed a permanent industrial base.

In May 1886 local businessmen organized the Businessmen's Association of Ann Arbor to promote business interests and encourage manufacturing. The organization was an effective force for only a few years and never did achieve its goal of attracting industry. Nonetheless, it was an important precursor of the modern Chamber of Commerce and paved the way for later collective action by Ann Arbor businessmen.

In August 1887 the city called a special election on a proposal by the Association to raise $5,000 in taxes for the purpose of "booming" the city. Voters approved the tax 230 to 78, but a number of determined opponents succeeded in getting a court injunction against its collection. After this setback the Association's influence diminished. Businessmen periodically revived the organization during the next decade but it was never quite as strong as in its first two years. With monthly meetings, more than 100 members, a number of hard-working officers, and committees on such specific subjects as sewers, road improvements, and the publication of literature "booming" the town, the organization did call attention to the implications of changes that were taking place in Ann Arbor.