I'm looking into buying an 2001-2007. My main concerns would be (1st) the transmission, and (2nd) Engine oil leaks. Reason being, I hear of trans problems with these. Is this a trans deficiency or maintenance related? We also used to own a 1992 Dodge Dynasty with 3.3L. It was still running okay at 250k but the thing couldn't keep oil in it in the way of bad leaks (not smoking). I was reading on Allpar that the early 3.3L engines had gasket deficiencies that were later revised. I'm still curious how these newer 3.3L/3.8L engines do for leaks when approaching 100k and beyond?

 

As far as gaskets on the 3.8L I don't think it is a deficiency but they just plain wear out and just need to be replaced. On the 3.8L the common ones I have found are the valve cover and oil pan gaskets. The 02 I have now also has a bad transmission gasket that needs to be replaced. On any vehicle the gasket just wears out over time and need to be replaced.
The oil pan gasket is easy to replace, when you need to change oil just drop the pan and replace the gasket. Front valve cover is pretty simple, the back one on the other hand is another story as it is not very accessible with the intake sitting right on top of it.
As far as the trans issues I think a lot of it is maintenance related.

 

Compsyn-I'd look for one with the lowest miles and newest build date. Around 100K you need struts, full tune up and valve cover gaskets, oil pan gasket and possibly the front crank seal.
On the tranny: inspect the fluid and ask for the service record on it. They will last if you change the fluid and filter regularly (30K miles). Good shopping!