Day-to-day information is increasingly being implemented in transit networks worldwide. Feeder bus service (FBS) plays a vital role in a public transit network by providing feeder access to hubs and rails. As a feeder service, a space-time path for frequent passengers is decided by its dynamic strategy procedure, in which a day-to-day information self-learning mechanism is identified and analyzed from our survey data. We formulate a frequency-based assignment model considering day-to-day evolution under oversaturated conditions, which takes into account the residual capacity of bus and the comfort feelings of sitting or standing. The core of our proposed model is to allocate the passengers on each segment belonging to their own paths according to multi-utilities transformed from the time values and parametric demands, such as frequency, bus capacity, seat comfort, and stop layout. The assignment method, albeit general, allows us to formulate an equivalent optimization problem in terms of interaction between the FBS' operation and frequent passengers' rational behaviors. Finally, a real application case is generated to test the ability of the modeling framework capturing the theoretical consequents, serving the passengers' dynamic externalities.