Analysts have explained why Osama bin Laden got caught. Bin Laden did not have enough contingency plans worked out to prevent his capture because he was careless.
Osama bin Laden should have known that foreign intelligence would try to track him down and he should have cut all connections with the outside world. Bin Laden should have left his second in command in charge of all of his organizations operations and authorized his second in command to operate under the bin Laden name.
"Bin Laden should have left several video and audio tapes with his second in command so he could have altered them to send out whatever message he wanted." said the intelligence mole.
Osama bin Laden should have purchased a multi-million dollar home in Bahrain and lived with unknown wives and the wives relatives. He could have gotten an operation to change his face and he could have gotten a new identity allowing him to walk about freely if he wanted to. He could have spent the majority of his time in his mansion retired while his organization would have continued on its own.
With no connections and with a new life, he could have died an old man without ever getting caught. It's hard finding someone that has no connections because it would be like trying to find a needle in a haystack.
He could have also had a panic room with an underground tunnel leading to a farm house with a car inside so he could have escaped in the event something went wrong.
He could have done everything normal to prevent looking odd and attracting attention. This is what chameleons do to hide from enemies. He could have had an old man at the compound that would have made friends with the neighbors to prevent neighbors from becoming curious as to who was living in the compound. He could have had 22 compounds and not lived in any one compound more than 2 years to evade any investigation done on any of the particular compounds. For example there is surveillance for 4 years on a compound and nothing is found, but 11 years later he moves back into the compound which has already been cleared by a previous investigation. He would have to live in his compounds in a round robin pattern. If you divide 22 by 2 you get 11 years which is the time period it takes to live in the same compound twice. Multiply 22 times 3 and you get 66 years which is how long it would take to live in the same compound 3 times which means that bin Laden would have died without living in any particular compound more than 3 times during his life, improving his odds of escape. The more compounds he has the more invisible he would become. For example, if he would have had 120 compound and he lived in each compound only one year then it would take him 120 years to complete a round robin in his compounds and he would have become invisible. If he would have lived in each compound only 6 months and you divide 120 by 2 you get 60 years which means he would spend less time in each compound helping him to evade an investigation at an accelerated rate improving his odds of escape at a higher percentage. He would have never lived more than 60 years which means he would have never lived in any particular compound more than once which would have made him completely invisible to his pursers. The compounds could have been as small as a single bedroom home or a three bedroom home to mix up the variety making detection impossible. It's like playing Russian roulette, nobody can be quite sure which chamber holds the bullet.
Osama bin Laden could have constructed an entire underground city near a mining company and his fighters could have lived there. The city could have had a sewage system that leads to a river with a large compost dump that fuels a methane electrical power plant. Then he could have build several hundred other cities across the Afghan Pakistan border. This could have helped him to avoid the drone and plane attacks.
One thing Osama bin Laden could have done was to send four spies to spy on members of his organization to find the moles but at the same time not removing the moles to keep his opponents satisfied while he would have maneuvered through his own organization to prevent capture. He could have sent a three year package of information to specific individuals that are not associated with the moles so he could have functioned in his organization while remaining invisible to infiltrators that are mingled inside his organization.
Any information that Khalid Sheikh Mohammed would have given his captors would have been irrelevant because it would have led to a dead end. His organization could have had fun using doubles to send foreign intelligence on wild goose chases that would always lead nowhere.
The worst mistake Osama bin Laden committed was to live in a country whose government was at war with his organization. He should have picked a country that was hostile towards his pursuers and non-dependent on his pursers to prevent his pursers from entering the region. Syria, Iran, and Libya would have been good places up until the recent uprisings. He should have had several hide outs in different countries with a private jet plane to transport him as conditions change.
He could have had an underground home under a small house just one home to the right of his compound where he could have spent the majority of his time and only walked to his compound at night dressed like a woman in a Hijab to pretend he was visiting the home on rare occasions, like when meeting a courier. When the raid would have occurred, he would have been nowhere to be found. His wife and children would have been safe in the smaller home or under the smaller home far away from the compound. The compound stuck out like a fortress and that could have been good if used for deception.
A good example was Hitler who faked his own suicide and escaped to raise his family in Austria. Hitler had face surgery to alter his appearance and he never ventured out of his home except to play in the yard with his children.