"Guess Where?" - a GCHQ word association puzzle (board game edition)

Question

_{This puzzle is part of the Monthly Topic Challenge #7: Board games.}

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Instructions (adapted from The GCHQ Puzzle Book (2016) and the introductory puzzle here on Puzzling Stack Exchange): The words in the following list can be partitioned into equal-sized sets depending on words associated with them; each set has its own word association method. This list is arranged so that these associated words are in alphabetical order. One of these sets is missing a member, so you have to work out where in the list the associated word fits alphabetically, and hence where the word itself should appear in the list. The list should be read from left to right and top to bottom and is only written in columns for convenience. (See the introductory puzzle for a more detailed explanation and an example.)

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The question to answer is:

Where does 'NUMBER' fit in the following list?

APPLE	CENTRAL	WESTERN	ILL	SLEEVE	GEO	FLOP
FREEZE	BASKET	TRICK	GREAT	ART	SKIPPER	HORSE
RECHECKS	CHEST	AVID	MIDDLE	COMPANY	STANDARD	VAGUE
TRAIN	SCENE	NEW	JAIL	TAX	PRAWN	RIDER
FILE	LOUD	ALMANAC	ARIA	DIGGER	CLUSTERED	SPORT
IRE	SHOP	ENTER	SOME	BEE	AM	CHARLOTTE
OM	WITTERS	WORKS	FLIGHT	FOOL	CRAMP	HIS

Crucially this time, every set relates to board games in some way.

In the first instance, please hold off posting partial answers unless you think you have found at least half of the correct word associations (although if you make it that far, why not push to complete the whole puzzle!). Thank you, and enjoy!

Answer 1

Categories:

1. Second word of Operation piece, take first word
2. First word of Risk region, take second word
3. Guess Who character with first letter removed, take original name
4. Second word of phrase whose first word is a chess piece, take chess piece
5. First few letters of Trivial Pursuit category, take category color
6. Synonym of Stratego piece, take original piece
7. Settlers of Catan resource with first letter changed, take original resource
8. Anagram of the name of a board game, take original name of game
9. Second word of Monopoly space, take first word
10. Word that rhymes with last name of Clue character, take original name

Matchings:

APPLE - ADAM’S - Operation
CENTRAL - AMERICA - Risk
WESTERN - AUSTRALIA - Risk
ILL - BILL - Guess Who
SLEEVE - BISHOP - Chess
GEO - BLUE - Trivial Pursuit
FLOP - BOMB - Stratego
FREEZE - BRAIN - Operation
BASKET - BREAD - Operation
TRICK - BRICK - Catan
GREAT - BRITAIN - Risk
ART - BROWN - Trivial Pursuit
SKIPPER - CAPTAIN - Stratego
HORSE - CHARLIE - Operation
RECHECKS - CHECKERS - Anagram
CHEST - COMMUNITY - Monopoly
AVID - DAVID - Guess Who
MIDDLE - EAST - Risk
COMPANY - ELECTRIC - Monopoly
STANDARD - FLAG - Stratego
VAGUE - GENERAL - Stratego
TRAIN - GRAIN - Catan
SCENE - GREEN - Clue
NEW - GUINEA - Risk
JAIL - IN - Monopoly
TAX - INCOME - Monopoly
PRAWN - KING - Chess
RIDER - KNIGHT - Chess
FILE - LIFE - Anagram
LOUD - LUDO - Anagram
NUMBER - LUMBER - Catan
ALMANAC - MANCALA - Anagram
ARIA - MARIA - Guess Who
DIGGER - MINER - Stratego
CLUSTERED - MUSTARD - Clue
SPORT - ORANGE - Trivial Pursuit
IRE - ORE - Catan
SHOP - PAWN - Chess
ENTER - PINK - Trivial Pursuit
SOME - PLUM - Clue
BEE - QUEEN - Chess
AM - SAM - Guess Who
CHARLOTTE - SCARLET - Clue
OM - TOM - Guess Who
WITTERS - TWISTER - Anagram
WORKS - WATER - Monopoly
FLIGHT - WHITE - Clue
FOOL - WOOL - Catan
CRAMP - WRITER’S - Operation
HIS - YELLOW - Trivial Pursuit