Doubling Process

Summarized here and well documented elsewhere.

For money:

• Look at position from opponent's point of view.  Are you sure the position is a drop?

• YES (a definite drop).  Then double, unless you are too good
•  NO (not sure a drop).  Proceed to next stop

•  Are you sure the position is a take?
• NO or Unsure.  Then double per Woolsey's Law.
• Discussion of Woolsey's Law.  Basic idea is
• If you are unsure then your opponent is probably unsure too.  It's always good to put pressure on your opponent.  Note opponent can't make a cube mistake if you don't give him a cube decision.  Send the sube and let him sweat it out.
• Position might be a proper double; then doubling is fine
• Position might not be a proper double; doubling still good idea since it gives opponent a chance to make a big mistake either by Passing a monster take -or- by Taking a monster Pass.
• Position might not be a proper double and opponent correctly takes (usually this means you are doubling early).  Even in this scenario, at least you are doubling as the favorite and your mistake may pay off for you anyway.  Also, oftentimes your opponent won't recube efficiently when the game turns around.  Meaning when things go bad, sometimes you get some free rolls with the cube on 2.
• YES.  Even if a for sure take, it might still be a double;  proceed to next step.

•  Position is a Take - evaluation of market losers.
• Discussion.  It might still be right to double even if opponent is taking.  Depends on how likely you are to lose your market.  In other words, after the next exchange of rolls will your opponent be dropping?
• O'Hagan's Law of Market Losers.  a method to approximate market loss
• Generally looking for minimum 25% market losers for a non-volatile position, -and-, you are still doing OK on the bad sequences.
• Specifically estimate Net Market Losers as follows: looking for minimum of 9 rolls
• Net Market Losers = (Your crushing rolls) - (Your anti-jokers) + (opponent's anti-jokers)

• Still not sure if you have enough market losers to double?  Consider these other factors.
• How difficult/ easy is the position to play for you and your opponent?  In other words, who is more likely to cough up equity in the subsequent checker play due to tough strategic decisions?
• A tough position for the opponent might justify an early cube to capture his further errors, while a tough position for you to play might argue for a hold and wait
• An easy position for the opponent to play might also argue for a hold and wait approach, especially if you think the position is borderline No Double / Take.
• Opponent specific weaknesses. Truly advanced stuff and definitely not my specialty.
• Is your opponent a dropper or a taker?  
• You might be wise to double late if your opponent always takes. 
• On the other hand you might be wise to double early (a "bluff double") if there is a decent chance your opponent will drop.
• Are you the much superior or weaker player?  Tread very carefully with this one.  
• I don't necessarily agree with this but some believe the better player should keep the cube value down and volatility low to maximize their skill advantage.  
• Conversely, it is argued the weaker player should cube aggressively to maximize the luck factor.  (As well as put pressure on opponent to drop a gammonish take since your better opponent thinks you suck)