This is mostly to help understand some differences if the ideas in both St. Augustine's Confessions and Dante's Inferno. By choosing where you would want to live to lead to why and how th historical context possibly makes a difference.
What is interesting about your topic is that both men lived during a time of cultural flowering that, at the time of their deaths, was beginning to decline. St. Augustine enjoyed the heights of the 4th / early 5th cent. Latin-Christian culture. When he died in 430, the barbarians were literally at the gates and the Western Roman Empire was about to fall. Dante inherited the glories of the High Middle Ages: the great mendicant orders, St. Thomas Aquinas andscholasticism, Chartres Cathedral, etc. When he died in 1321, the cracks in the edifice were widening: the Avignon residence of the Popes had begun, the Black Death was on the horizon, and the rather wretched 14th century would end with the Great Western Schism and Hundred Years War still in progress.
One good reason to pick Dante's time is not only that his native Florence and wider Italy was on the brink of or just beginning the Renaissance (in the sense of being a flowering of advanced medieval culture), but also that Dante enjoyed all of the progress made from St. Augustine's time to his own. For example, the influence of Aristotle as a check to Augustinian neo-Platonism is a reason to choose the early 14th cent.
As for the daily life of a typical person, I bet we moderns would find both times pretty rough.
Renaissance for me, largely because I just love the period of history and the art, literature and architecture, though I agree with other editors who highlight the downright nastiness of life that probably existed in both periods.
Since Shakespeare and Elizabeth I lived during the Renaissance, I think I'd have to choose that era. But have you ever seen the BBC program "Worst Jobs in History"? Neither era would have been very pleasant to live in. Take a look at what it was like:
Jeez, those are my choices? I suspect I'd quickly be dead in either one of them.
Okay, enough waffling. I guess I'd have to choose Dante's time, but mainly due to whether war was going to break out, and if Rome was failing or still standing. (As you can see, I'm basing this completely on life and death, and order/chaos; those trump philosophical issues for me.)
Philosophically, I suspect it would be easier to get along in Augustine's time; fewer ideological clashes and more space to escape them.