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Partial Answer:

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

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

  3. That's Ben Petrick at top of picture B.1999 was only Rockies team 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 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 looks like bottom of picture D