The seminal architecture of machine self-reproduction originally formulated by John von Neumann underpins the mechanism of self-reproduction equipped with genotype and phenotype. In this thesis, initially, a hand-designed prototype von Neumann style selfreproducer as an ancestor is described within the context of the artificial life system Avida. The behaviour of the prototype self-reproducer is studied in search of evolvable genotype-phenotype mapping that may potentially give rise to evolvable complexity. A finding of immediate degeneration of the prototype into a self-copying mode of reproduction requires further systematic analysis of mutational pathways. Through demarcating a feasible and plausible characterisation and classification ...