Everlasting inflation has far-reaching implications for cosmology and the standing of self-localizing inferences made by observers, which have been subjects of renewed interest in light of the growing acceptance of theory landscapes and the attendant anthropic arguments. Under what assumptions and to what extent does inflation generically produce an eternal “multiverse,” without fine-tuning with respect to measures over the space of inflationary cosmologies driven by a single minimally coupled scalar field? We address this and related questions with numerical simulations of inflationary dynamics across populations of randomly generated inflation models, instantiating a few particular simply-defined measures.