Green’s Dictionary of Slang

hopscotch v.

1. (US Und.) to take a chance.

[US]Wash. Times (DC) 14 Sept. 10/3: Hopscotching — Taking chances.
[US]F.H. Tillotson How I Became a Detective 92: Hopscotching – Taking chances.
[US]St Louis Post-Despatch 16 Jan. 25/2: This joint isn’t doing any hop-scotching (taking chances).

2. (US Und.) to move frequently from place to place.

[US]Jackson & Hellyer Vocab. Criminal Sl.

3. (US Und.) to travel the country with a confidence game.

[US]D. Maurer Big Con 299: To hopscotch. To go on the road with a confidence game.

4. (US) to have many sexual partners.

[US]L. Wolf Voices from the Love Generation 138: ‘You went through a stage of what he called “hopscotch?”’ [...] ‘You can sincerely ball a lot of people.’.

In derivatives

hopscotcher (n.)

1. (US Und.) a peripatetic confidence trickster.

[US]J.E. Dadswell Hey, Sucker 160: The next week a hopscotcher came along.

2. (US Und.) a carnival showman who moves from place to place.

[US]J.E. Dadswell Hey, Sucker 100: hopscotchers ... showmen and concessionaires who move about the country independently of any one organization.