A simple guide:
Why flash?

More detail. More drama!
Kyoto flash. #cindyproject Street portrait with RICOH GR II shot with a flash at a gas station in San Mateo, California. Flash, blur. Tokyo flash, RICOH GR II. Escalator. Mumbai, 2011. Leica M9 x Flash Street portrait, woman looking right. NYC, 2015. RICOH GR II x FLASH Seoul flash, grimace. African-american cop cutout. Downtown LA, 2013 #flash #portra400 Flash photo I shot while chatting up a gentleman in Paris, catching his laughing gesture. Film Leica MP, f/8, flash at 1/8th power, 1.2 meters Long-distance flash photo, film Leica MP, Kodak Tri-X 400 film. Red hair, greenbackground. Philly, with flash. 2013, Kodak Portra 400 Flash street photograph, shot on film, flash, 1/15th shutter speed. Eric Rivera, street portrait with cigar. 1 meters, with flash, Leica M6, Kodak Portra 400, 35mm lens Tokyo woman with hand. 1.2 meters, flash, Kodak Tri-X 400, Leica M6, 35mm Smoke with flash. The smoke adds to the mood. Jazz man with trumpet and light trails. Shot with flash at 1/15th of a second Tokyo. 2015. Shot with RICOH GR II in P MODE, with flash, through a translucent umbrella. Philly. Portra 400 and flash. Red hair against green background.
The simplest flash possible
First step:
The simplest, smallest, and most automatic flash, the better.
For example, RICOH GR II in program mode with the integrated flash.
Experiment with distances
Photos from my SUITS project. Some shot on film Leica + Kodak Portra 400 flash + Leica SF20 flash. Also a few on RICOH GR II on flash.
Suits. Wall Street American flag. Suits street photography flash Suits nyc. Flash suits. NYC. Suits nyc. Portra 400.
Practice with in-animate objects and people.
Experimentation is key
You never know what a flash street photo will look like until you shoot it. Thus, just shoot in order to see how the photograph will look like with a flash.
Downtown LA, 2016 Downtown LA, 2016 / PENTAX 645Z ERIC KIM x PENTAX 645z ERIC KIM x PENTAX 645z PENTAX 645Z MARILA MARDRILES. Downtown LA Street Portrait with Pentax 645z
Experiment with different cameras and formats
For example experiment with your iPhone, integrated flash on your Fuji or RICOH GR II camera, etc.
Fujifilm XF10 with flash. Espresso machine Processed with VSCO with a6 preset Current setup: Fujifilm XF10, SR+ Mode, ERIC KIM WRIST STRAP MARK II Selfie with Fujifilm x100T
Monochrome vs color?
Dark Skies Over Tokyo, 2017