Quicken's menu structure leaves a lot to be desired. All of the most frequently-used options are under the Features menu or the Reports menu. Because a large number of features are contained in these two menus, most selections are two levels deep in the menu structure. Using pull-down menus that are two levels deep is challenging for users, since they must keep the mouse in a narrow track in order to navigate the second-level menu. Fitt's law (Card and Moran, 1986) predicts that this will be much slower than using a single-level menu, decreasing efficiency.
Many of the items on the Features menu (and some on the Reports menu) have only two items at the lowest level. This center-heavy menu structure ignores the results found by Norman (1991), which states that menus should have the most choices at the top level and at the bottom level.
The Lists menu is a menu of everything that doesn't get used very often. Users seldom create new accounts, categories, classes, or types of securities. Many of the items found on the Lists menu are accessible elsewhere (ie. new accounts can be created from the account register), so the Lists menu hardly ever gets used.
When the program is closed, the states of some of the open screens are saved (such as the account register and the report generator), but other screens are not considered important enough to be saved. This violates Cooper's (1995) principle "Any command is a working set candidate." When a user adds a screen to their working set (the set of items they normally use), the program should keep track of this fact, and open that screen for the next session.
The entire state of the system should be saved when the program is closed, since users tend to perform the same operations every time they use the program.
Card, S. and Moran, T. (1986) User Technology: From pointing to pondering. in Proc. ACM conf. on History of Personal Workstations, Palo Alto. ACM.
Cooper, A. (1995) About Face: The Essentials of User Interface Design. IDG Books Worldwide.
Norman, K. (1991) The Psychology of Menu Selection. Ablex Pub. [Chapter 9]