The PICTURE-C balloon mission launched on its second flight from Fort Sumner, NM on September 28, 2022. During this flight, PICTURE-C, which consists of a 60 cm off-axis telescope feeding a vector vortex coronagraph, demonstrated the first high-contrast dark hole from an observatory in a near-space environment. The coronagraph achieved a modest broadband (20%) contrast ratio of 5 x 10-6 , with performance limited by dynamic pointing transients. The low-order wavefront control system achieved optical pointing stabilization of one milliarcseconds RMS for intervals of up to 30 seconds between these transients. This paper will summarize the second flight results and present the development path for PICTURE-D, the next generation direct imaging balloon mission.