It sounds like he needs something upright and comfortable, not too hipsterish.

The Trek Soho S is good choice but could be a theft target. Craigslist is a good place to start to look for something gently used but stylish.

You really cant beat singlespeed for ease of repair and maintenance. You can beat it with a fixed gear but you're not cool enough for one of those :-).

Go with the Soho and free yourself from automotive prison.