Well I appreciate all the input. Im taking my truck in tomorrow and he's going to do a free diagnostic on it. I guess I'll just keep my fingers crossed. I traded my 02 gsxr 600 for this thing and so far I havnt had any regret so hopefully it stays the same.........
I took the truck to a recommended transmission shop in town. From there, they were ran a full diagnostic on the transmission. No Error's/codes from the scanner and no noticeable transmission wear. They actually had mentioned It looked really clean inside the tranny and he said thats a usually a good indication its been rebuilt. They had also mentioned it appeared a "shift kit" had been previously installed but had been taken out.
Also regarding the Over drive issue, the mechanic did a lil research and did indicate that the automatic over drive kicks in when I think he said transmission reaches 50 degrees.
So they ended up doing a standard transmission service which he said was definitely needed. When I got the truck back, It shifted much much smoother and overall drove better. I took the truck out of town (600m round trip) and had no issues what so ever. I still LOVE my dodge!