Green’s Dictionary of Slang

1. (US) to treat others meanly and miserly, thus to be petty and irksome, to eat away at.

1913		Wash. Post 20 Apr. (Misc. section) 3/6: ‘They nickel and dime you to death these days,’ ‘Alex’ informed a visitor the other day. ‘Why, if I was to get a $5 tip now I would retire.’ .
1961		(con. early 1950s) J. Peacock Valhalla 439: Well, at least [...] you ain’t nickel-and-diming me to death for a change.
1976		Time 28 June 38: He wasn’t the sort to nickel and dime his women—except possibly his wives.
1978		J. Webb Fields of Fire (1980) 336: It was the worst shit I ever been through. Nickel and dime. Nickel and dime. They ate us up.
1980		(con. 1973) W. Sherman Times Square 165: Did ya see how he tried to nickel-and-dime us down. That guy’s got thousands and he’s complaining.
1990		M. McAlary Crack War (1991) 74: We can’t give you any money. We’re nickel-and-diming you to death.

2. (US) to carry on a small, cash-starved business, to manage with little money; often as to nickel-and-dime it.

1973		Newsweek 5 Mar. 24: [He] worked his way through New York’s Richmond College with the help of G.I. benefits and part-time jobs. [...] ‘I nickeled-and-dimed it all through college.’.
1989		(con. 1982–6) T. Williams Cocaine Kids (1990) 55: They are hooked in some kinda way to the life, the excitement, the nickel-and-diming.
1994		N. McCall Makes Me Wanna Holler (1995) 249: A lot of the Muslim men seemed unable to get beyond nickel-and-diming, selling jewelry, fruit, and bean-pies on the streets.
2001		Barbara Ehrenreich [title] Nickel and Dimed: On (Not) Getting By In America.

3. (US, also five-and-ten) to beg on the street.

1942		Berrey & Van den Bark Amer. Thes. Sl. § 487/3: Nickel-and-dime, to beg on the streets.
1949		Monteleone Criminal Sl. (rev. edn).
1956		‘James Updyke’ [W.R. Burnett] It’s Always Four O’Clock 35: Royal [...] asked: ‘Say, have you fellows got any loose money?’ Walt recoiled. [...] Hollywood was full of bums who five’d and ten’d you to death.