I'm in Portland Oregon and I need to find a good and reasonable mechanic. I don't trust the Chrysler dealership, they can't do a simple oil change properly. However, they did inform me that the car has an oil leak and possible transmission leak but that's all they said. (this was in Sept 2014). If anyone can steer me in the right direction, it would be greatly appreciated. I don't want to sound like an uninformed female, I know a great deal about this car and I do my research, unfortunately this time I'm clueless. Btw: 2005 conv.

 

Probably the 13 pin data Port connector on the transmission it's a common leak the parts run about 12 to 13 bucks and while you're at it , it's a good time to change the transmission filter and fluid that's a little more expensive, at the Chrysler dealership and Mercedes dealership the transmission fluid runs about $21 a quart but you can get the transmission service kit online a lot cheaper. Or you can order it from Rob at needswings.

 

Before taking your car anywhere for "repairs" Pull the plastic engine shield off under your car and look for oil. See any?
If yes it could be value cover gaskets. Not likely oil pan, but anything is possible. If No there are inspection plates on the bell housing. Remove plates and swipe your finger inside. Oil? Could be rear main seal or seal plate. If No, Dealer is looking for easy money.
You also have transmission cooling lines that run from the transmission to the radiator. Check them out. Leaking? You found your leak. No then it is as Post #2 suggests, which most likely is the problem, BUT if you don't won't to be totally ripped off >> know where the leak is before you take it anywhere for repairs.

There are probably 40 shops that repair cars in the city nearest me: From personal experience I can trust only one with my cars or truck. Just one! Good Luck.

 

Trans fluid is red engine oil is dark brown or black probably the data port connector leaking on trans easy cheap fix.