Was gonna tell you to just put a new gm starter on it but let you figure that out on your own. When you pulled the starter out did you shake it like a shake weight and if you did did it sound like something major loose inside of it .?
On your shifting who did the tune? At what rpm are you letting off the throttle at? My tune guy sets it at 6500 rpm at wot that means if you have it floored it will not shift until 6500 rpm you have a 4l80e in your swap ? If so first is long so waiting on 6500 rpm and then to let it hit second is a little scary my tune guy said this to me it shifts as per throttle pedal so if you give it the beans that's what your gonna get. Other than that its the only help I have for ya.
Tommy