Partial Answer: 

1. Pretty sure [Derrick Gibson][1] is at bottom of picture A.

2. [Todd Helton][2] as you mentioned middle of picture B.

3. That's [Ben Petrick][3] at top of picture B.[1999 was only Rockies team][4] with Petrick, Gibson and Helton - I looked at autographs for all on roster and only could confirm those three. I'd encourage @Lacey or others to research those names to see if there are any other matches.  You might also look for coaches from the 1998 - 1999 seasons.

4. [Manager, Jim Leyland][5] looks like the bottom of picture B (though worn its pretty close to samples linked in his name),

Less certain but based on 1999 Rockies

[Hitting coach, Clint Hurdle][6] looks like bottom of picture D