We bought our Town and Country used from our local dealer 6 years ago. I was nervous to take it on, having heard so many bad things about Chrysler products, but I have to say that I have been pleasantly surprised by the reliability of the van.
We did have odd water pump issues (we're on the third water pump) although we don't tow anything. But that's really the only major problem we've had with the van.
The transmission is still working fine, as does the air conditioner, and even the power door, and the van still looks great after all this time!
I did notice that we do go through brakes a little faster in the van, and if you're looking for good gas mileage, this thing sucks gas like a pig, even with the 3.3 V6.
Otherwise, if you are willing to stick to the maintenance schedule, this could be a good affordable family vehicle for you.
I know a lot of people with Town and Countrys near the same year as mine that are still dependable and on the road, and they too keep to the maintenance schedule. So don't push off the maintenance!