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After superheroes are forced to retire, Bob has to get a job in insurance, which he clearly hates.
During his original superhero days, something was paying for lifestyle, which included an incredibly advanced supercar. He makes some endorsements, but there isn't any indication they'd be enough to support himself, at least at the beginning of his superhero career. I don't think there's any mention of the government supporting him, so how did he make money?
There are a considerable number of money-spinners on his wall of fame
The Mr Incredible Cadets
An album of covered songs ("Mr Incredible Sings...") which, according to the Incredibles Essential Guide went 'quadruple platinum'
Merchandise aplenty (lunchboxes, patches, pez dispenser, branded Rock 'Em Sock 'Em Robots game, etc).
An action figure and various toy cars
A branded cereal ("Incredible Pops!")
Mr Incredible Official Fan Club
A Mr Incredible branded comic book ("The Most Incredible Comic on Earth!")
Endorsements ("Bonhomie - It's the car Mr Incredible would drive...")
We learn from the commentary track to "The Adventures of Mr Incredible" that he's protective of his intellectual property (if not especially worried about quality) which strongly implies that he's getting a cut of any sales that are made with his likeness.
Note that Mr Incredible's super-car (the Incredibile) was supplied by the National Supers Agency. There's also a magazine feature about the Incrediboat and he's, presumably, receiving other payments and equipment from them.
