Systems for and methods of conducting field assessments utilizing handheld data management devices are diclosed. Methods and systems for executing field assessments use handheld devices provide assessors portable access to industry-specific programs and data useful in carrying out a field assessment. Field assessment data synchronization and/or delivery is enabled using wireless capabilities resident in handheld personal computing devices. Data may be synchronized with a server over a network using wireless radio transmission, or directly to a computer workstation using wireless infrared or radio transmission or connected means (e.g., modems, cradles, docking stations). It is another aspect of the present invention to provide for two-way communication between remote computing means (e.g., servers, desktop computers) and handheld data management devices to facilitate real-time access to remote programs, assistance and/or information related to the field assessment being undertaken by using a handheld data management device user.