The League of Detectives

In Order from Left to Right we have the strengths and weaknesses of:
SHERLOCK HOLMES:
William Sherlock Scott Holmes is the archetype for the detective. His deer stalker is the first image conjured up when a detective is mentioned. He is sly as a fox, quick as a whip and intuitive to a point. Clearly not someone to mess with at all. He is a patient watcher standing midst over the sea of "goldfish" that is London.
Strengths:
Mind Palace: He has ". . .soaked up every fact under the sun in there."
Boxing: Proficient bare-knuckle fighter.
Knowledge: Everything (See Mind Palace)
Sword and Cane: Expert Swordsman, especially when improvising with a cane.
Disguise: Pretty much a Master of Disguise
Weaknesses:
Friends: Though he claims he has no "Friends" they make quite a target for Holmes' enemies, (I.E. John Watson, Mrs. Hudson, etc.)
Mycroft: The only person really smarter than Sherlock is his brother Mycroft, luckily he sits on Sherlock's side.
Moriarty: Though Sherlock did best James Moriarty, he was his toughest challenge yet.

BBC's Sherlock
THE QUESTION:
Charles Victor Szasz (No relation to Mr. Zsasz from Batman), also known as Vic Sage is a highly outspoken and aggressive investigative journalist. His identity hidden by a Pseudoderm mask and tantalizing methods in hand, he sets out to make his town called Hub City a better place. He is the only one on this list without a live action movie.
Strengths:
Pseudoderm Mask: A compound originally used for bandaging wounds, the mask allows him to filter air, see clearly and hide his identity, while providing a somewhat intimidating facade with no face.
Specialized Belt-Buckle: The Belt Buckle releases a binary gas, molding the mask to his face temporarily and changing his hair and features for disguising purposes.
Conspiracy Theorist: Usually conspiracies are fake, but in a fictional universe they more than often prove true. His foresight for these could come in handy.
Martial Arts: Trained by Lady Shiva herself, he knows how to hold his own in a fight.
Weaknesses:
Easily Killed: I suppose all of the people on this list are killable, but The Question is by far the easiest to kill. He did eventually die of lung cancer.
Conspiracy Theorist: A double sided coin. Though one conspiracy may be true, he would more than often get tangled up in one that may not be true.
(Let it be said, what he lacks in physical stature, he makes up for with his uncanny detective work and impeccable swagger).

The Question, as portrayed in New 52
BATMAN:
Bruce Wayne, eccentric billionaire by day, brooding hero by night. He is the Batman. He is by far one of the most recognizable superheroes, which is amazing because he literally has no superpowers. When not prowling Gotham City he spends his leisure time fighting along side the godlike superheroes of the Justice League, or commanding the more "under-the-radar" team of heroes knows as The Outsiders. He is no joke, despite the costume.
Strengths:
Martial Arts: He knows literally every form of martial arts. During a period of time he abandoned his home and searched the world to reach peak human condition and master all the ways to kick butt.
Tech Support: As he is head of Wayne Industries he has a vast collection of pretty much everything supplied by Lucius Fox. Everything from the Superman-killing Bat Armor to the very specific Bat-Shark-Repellent. He is prepared for everything.
That Utility Belt: Pretty much has anything for any occasion, enough said.
Intellect: It has been under debate for a long while whether Batman is smarter than Sherlock and I may go on a limb to say that Batman may be just under Sherlock if not at his same level. They have both solved the Jack the Ripper case in two different iteration and put him to justice, so I see them as the ultimate duo.
Weaknesses:
Mortality: He is human. Merely just a bullet could kill him, or old age at that. But let it be said that "The Batman" is an idea, to truly kill him you would need to kill the idea.
Friends: Batman has said himself that it would be particularly easy to get at him if one threatened Alfred, Robin, Barbara Gordon or Wonder Woman.
Not Having A Plan: Actually no.....he's got a plan for that.

Batman, from Arkham Origins
RORCHACH:
Walter Joseph Kovacs is the identity of the Watchman Rorchach (pronounced Roar-Shack). Though bearing a striking resemblance to The Question, is a much deeper hero. Abused as a child and very intrigued by a chemical compound designed by Dr. Manhattan, he prowls New York City with an ever changing Rorchach inkblot on his mask.
Strengths:
Acrobatics: He can jump roof to roof, scale buildings, and land flat on his feet with out making a noise.
Hand-to-Hand: Advanced street fighter hardened by prison
Espionage: Gifted at spying on friends and allies to confirm his suspicions
Will: With all the awful things that have happened to him he has an unquenchable thirst to punish all crime.
Weaknesses:
Mental Illness: His mind is at war with itself and he is not a dependable individual socially and should really be used only in dire circumstances. This is really his only weakness, but it's a harsh one because he is so unstable and could likely at any moment explode and kill everyone, including the people on this list.

Rorschach, as portrayed in the 2009 film Watchmen
THE SPIRIT:
Dennis Colt dons the obligatory trench coat as the last member of our super sleuths. Dennis or Denny was a cop who was fighting Dr. Cobra and was splashed with a deadly chemical sending him into a coma. They believed him dead and 24 hours after he was buried he woke up. He set up headquarters under his tombstone and fights the crime of Central City.
Strengths:
Uncommon Strength: A little bit like Jean Valjean from Les Miserables. The Spirit has uncanny strength for a man of such stature.
Revive: I don't know how, but since he awoke from his slumber The Spirit can revive from the dead regardless of how he was killed.
Vehicle: He has a plane that turns into a car. . . . . .none of the others have anything that cool.
Weaknesses:
Honestly..........he can revive himself regardless of how he is killed. If you want him dead you'll just have to wait it out.

The Spirit from his movie in 2008
Let it be said that these men all have the credentials of legends under their belts. They are all capable of some serious stuff and yet I feel I misrepresented some of them (ahem........Question and Spirit). To clarify, they are all extremely intelligent and very adept at what they do. A team-up between then, though seemingly impossible, would be the event of the century (completely smashing Batman v. Superman any day.) In fact they are all DC comic-book characters, but the one thing that could perfect a lineup of men such as this is Sherlock Holmes. Let me know if you agree of disagree with any of this, I saw that photo on the web and decided it would be interesting to expound upon.
Thank you all so much.