Modeling is a complex and central activity in many domains. Domain experts and designers usually work by drawing and create models from the middle-out; however, visual and middle-out style modeling is poorly supported by software tools. In order to define a new class of software-based modeling tools, we propose a scenario and identify some requirements. Those requirements are contrasted against features of existing tools from various application domains, and the results show general lack of support for custom visualization and incremental knowledge specification, poor handling of temporal information, and little generative capabilities. Satisfaction of the requirements proved difficult, and our first two prototypes did not perform well. A new and streamlined prototype is currently under development: it should enable some useful form of middle-out modeling. Application domains will range from visual knowledge representation to objectoriented analysis, and graph rewriting.