I was pretty sure the answer to #4 was Dwight Gooden and Gary Sheffield from Tampa but I was wrong. I think the correct answer is Sheffield and Derek Bell (I used Wikipedia). If anyone is curious, I discovered Baseball Almanac has a list of 13 players who were in both the LLBWS and the World Series, now 14 with Bellinger.
The correct answer to 4 is indeed Derek Bell and Gary Sheffield. The answer to 2 is not Boog Powell. His Lakeland FL team lost before the championship game.