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Jane Jacobs in her seminal work Death and Life of Great American Cities (1993) titled a chapter of her book, The Kind of Problem a City is, and in it, discussed how a city should be understood as a situation of a complex nature. Observers of cities have, from as early as the Renaissance, attempted to identify the kind of problem cities are by comparing them analogically to a variety of subjects and artefacts. This has been done to discuss and extrapolate the issues surrounding what a city is in a multitude of ways and to better grapple the complex issue that the subject of cities pose. However a single explanation or analogy will likely ever satisfy the discourse as a fundamental framework. The difficulty in reaching a single framework is twofold. Firstly cities and the way cities are inhabited, changes and evolves over time. And, secondly, and perhaps more problematically the way we think about them and come to know them also changes and evolves. To put simply, there are epistemological struggles in urbanism that require attending if the complex issue of a city is to ever be reconciled. Empirical observation and interpretation of the city – an alternative technique at the time of Jane Jacobs writing of Death and Life of Great American Cities, is the recording of events and occurrences and looking at how and why these might arise. This is what separated Jane Jacobs from the common school of thought at the time. It was a departure from the overly simplified rational logic of the Modernists – a school of thought made widespread by its success but had extended passed its limitations. Jacobs had observed an underlying and intricately delicate balance that had evolved out of the complex connections in the diversity of the people and their spatial conditions within a city; a balance she called a "ballet of the street". To Jacobs the Modernists obsession of order through ‘orthodox’ planning and zoning that had sought to impose homogeneity over populations and areas simply did not observe or appreciate the complexity of cities and streets that created the very emergent qualities of healthy urbanity. Qualities that Jacobs had noted “ought to be cherished and celebrated”. This thesis therefore delves into contemporary techniques of understanding and observing cities particularly by digitally modelling and dissecting areas to better interpret and come to know the existing urban condition so that we may build better knowledge foundations for urban discourse. It will identify that through changing and diversifying paradigms and epistemologies of knowledge, our perception and our a posteriori ability to identify the kind of problem that cities are, is not static and that it develops and evolves from generation to generation. This is a necessary change that occurs in order to revaluate and solve certain kinds of problems and puzzles that pertain to the generation taking place. The significant point that I argue is that such change, at an epistemological level, is inevitable and necessary. And as these evolving epistemic foundations can dramatically alter the significance and legitimation of the entire body of urban knowledge, then a continuing critical discussion of the contemporary state of epistemic urbanism or a philosophy of urbanism is a necessary task for identifying and framing the kind of problem a city is. Furthermore, this thesis will outline methods of (re-)framing those foundations to better carry over constructive and applicable knowledge that will help build new and contemporary understanding of cities and urbanism. These frameworks and methods will be tested through hypothetical re-design of existing city fabric in order to help realise the applicability of new research techniques.

The Kind of Problem a City Will Always Be: A Study of the Epistemological State of Urbanism and the Kind of Problem a City is