2000 Silverado Shut off while driving...Please help
 

Let me start off with some basic info first:
My dad gave me his 2000 Silverado (1500 I believe) 6 years ago when he bought a new model. He is anal retentive about oil/fluids/ and tires being rotated on time. It's never been in a single accident and the most work it's had to have done was this January and May of 2015, first time was the power steering hose and this last time was the power steering box. The battery was replaced 2yrs ago as that had never been replaced and finally died. It has 209,250mi (it had 191,000 when given to me.)
After getting Big Blue back this last time, my truck sometimes starts up when you first try to turn him on, but it seems like if I drive less than half a mile and say stop for gas, sometimes I have to turn the key the most I counted, 10 times. Then the past Friday, all was well and then as I made a turn everything shut off. I mean no lights, sound, movement, etc. I was able to quickly put him in park and restart in the nick of time. I get it about 2min away at my parents, and before I get all the way in the drive, same thing, complete shut off except this time I had to turn the key multiple times to get him on again. My dad followed me back to my house (1mi) and I park it. He calls the next morning to say there's oil all over his driveway starting from my turn into and where i finally get it parked there. Go to take it around the block the following afternoon just to see and nothing happens so i decided to take it to the gas station across the street and low and behold he shuts off while I'm driving.
During these times I wasn't ideling for even a second, it scared me each time. I really don't know a lot about cars so this is the best info I can give for now. Please help me help my truck feel better!! I love it more than anything!
Thanks!

After hearing that there was oil all over your father's driveway, did you check the oil level in the truck? Was it low or was it OK? The other problem sounds like it could be a loose or corroded battery cable. Both cables have to be checked at the battery and at the other end.