Wolverine is the ultimate badass. Any man who routinely is shot in the face and regards chopping someone in half as part of a standard work day is pretty damn badass. When faced with an unstoppable army of thousands of undead ninjas, there is no man I would rather have by my side (actually in front of me) than Wolverine.
But he's not a man I would want managing my 401k.
Throughout his long, long life Wolverine has shown very little interest in matters of an economic nature. He's spent most of his time living in cabins, hovels, and sleeping in the beds and houses of others. His worldly possessions seldom exceed the clothes on his back (usually a jumpsuit made of spandex or leather), a cache of cheap cigars, a motorcycle, and a six-pack of beer. This is the sum of the worldly possessions he has accrued in over 100 years of life. Granted, a large part of this life was spent being mind controlled and experimented on, but in the years since he's escaped from Weapon X, Wolverine has made a series of life decisions which placed him in financial jeopardy.
First, he left employment with Department K and Alpha Flight to become a member of the X-Men. This provided Wolverine with food, shelter, and access to Jean Grey but denied him the benefits of being a government employee. That is, of course, assuming that government secret weapons have access to excellent health care and a pension program. But since his time with the X-Men Wolverine has consistently shown he's just not interested in money. He became involved in the criminal syndicates of Madripoor, but only did so out of loyalty to the guys who ran his favorite bar and because he was attracted to the local boss, Tyger Tiger. At nearly all opportunities he avoided any financial gain through these criminal activities. He even became a mob enforcer later in life. But this was only so he could reorganize the structure of the mafia family to his personal liking. He became an agent of S.H.I.E.L.D. and left shortly after the purpose of his membership changed. He never saves money and doesn't place himself in a position to acquire assets.
But despite all this, Wolverine has stayed afloat. He's been able to purchase the things he wants when he needs to purchase them. It seems like beer, gasoline for a Harley, and plane tickets to Japan are always within his budget. Of course it's possible that he purchases everything with credit. And then when AIG sends him a bill, he mails it back with a picture of his claws covered in blood. All debts would be subsequently cleared.
But regardless, Wolverine's spartan lifestyle seems to be enough to sustain him. He has plenty of free time to right random wrongs, save the world with 3-4 teams of heroes, and sleep with the dozens of women who have shacked up with him over the years. Though Wolverine may not be very rich in the traditional sense, if he maintains his current lifestyle, it seems like he is managing his money quite well. He doesn't spend frivolously, he knows what he wants, and he makes sure that he gets it.
Of course if Wolverine ever tries to settle down and lead a normal life, his lack of assets could be disastrous. See "Old Man Logan" for the consequences of not saving enough to pay your rent money.