I have a 2003 Durango and when it hasn't been running for a few hours and I try to start it, the oil pressure gauge doesn't go up and the Check Gauges light comes on in the Information center. If I shut it off and restart it, then it works normally, but almost 100% of the time, will not engage on the initial start-up.
Any ideas?

 

I'm thinking the oil pump may be on it's way out. Before you go replacing it though check out the oil pressure sensor first.

 

might be a oil pressure sending unit going out, i would maybe check that, or get a mechanical gauge on it to check what the pressure REALLY is