You can get amazing old houses for amazing prices in those towns southwest of London. I sometimes look at the MLS website and weep.
The main streets have that classic southern Ontario charm, and it's palpably warmer and less snowy in winter than the GTA and the extended greater Golden Horseshoe.
The problems with the area as I see it are:
1. It's flat. So, so flat. As in: no hills. Whatsoever.
2. It's isolated. Chatham is an hour from London and an hour from Windsor, and at least two and a half hours to the GTA. During heavy GTA traffic times you're looking at three and a half hours to downtown Toronto. That's not a day trip anymore. Detroit is not an alternative to Toronto by any stretch of the imagination, and the thought of it being my nearby metropolis is depressing.
3. I've heard that southwest of London the people tend to be a little bit more American in character and a little bit less Canadian. That's a complete deal-breaker. For me, anyway.
And yet, look at the kind of place you can get for $359,000 in Chatham:
This one in Ridgetown is $209,000:
It's like they're giving them away!