So I have a feeling my trans is on it's way out in my 99, so rather then worrying about the cost to replace and fix it I have found an 08 1500 I am looking into trading my 99 for.

So my question is, what are your thoughts on the matter...

The 08 has 40k one owner and is in pristine condition. But what sort of problems are common in this year? Am I going to be getting into the same issue a few years down the road?

 

well you are talking about 11 years since the 99 was built....you didnt tell us the motor and none of us have owned the 06-08s long enough to tell you about down the road, but as of now there are a few issues

From RF:
-retainer clips in anti spin diff
-leaky rack and pinion
-warped rotors
-hemi tick
-i think the 4.7's had sludge issues, and head gasket problems..??

 

I would say w/ the lil info that you gave us on the 08' (price, engine...) that you would sure as hell be better off w/ a truck that is a few years old as opossed to a truck that is 11 years old. If it is in pristine condition the owner prol took good care of it. Like any used vehicle purchase weigh your options and analyze the risk. IMO go for it and if ure worried about problems look into an extended warranty. I purchased a bumper to bumper for the life of my loan just in case.