I think I have maybe a different view than others. If you live in town and won't be driving the diesel more than 5-10 miles, in-town commuting most of the time, I wouldn't recommend a diesel. It's hard on them to not get out and be driven for longer distances/times. But I grew up a diesel mechanics daughter, so maybe that just rubbed off on me.
Don't get me wrong, I love my diesels, both the newer F-350 we have, and our old Dodge Cummins. But we have always lived in the country here in MN and in MT, so I've not worried too much about short distance driving. As far as starting in winter, ours have always started, but I do carry an extension cord when we head west in winter and stay at hotels with plug-ins in the parking lot if it's supposed to be real cold overnight. I've never had a problem starting either one at -35 when plugged in and anti-gelling dumped in the tank (some places I can only get #2 diesel, not mixed).