Abstract: The web as a paradigm of computing has introduced fundamentally new possibilities for creating, driving and achieving differentiation in the business domain. These in turn have resulted in a greater emphasis on reducing the time to market and increased application complexity. Innovative practices such as iterative development and the use of software components for application development have had significant impact, although with mixed results, in practice. In situations where application design and implementation are based upon a novel 'core idea' to be developed in a telescoped time frame, the implementation is constrained both by the time factor and the need for integration of third party components and solutions into the application. Furthermore, the proliferation and relative instability of technologies and tools adds another dimension to the problem of determining optimal application architecture. The present paper analyzes these issues and explores their important causes and consequences. Some pitfalls of traditional approaches in the development of systems under time-constraints and dynamic coupling between evolving requirements and application design are illustrated. Using examples of developmental experiences in projects, a few common points of approach are brought out to understand, adopt and implement a modified process to cater to such practical situations.