I was thinking about this technique recently, and something occurred to me: the Painting the Scene Technique is particularly good at conveying the feel of a film montage.
It feels like a montage, because we’re going around the table and getting multiple, fairly quick “takes” on the scene. A single GM relating details just can’t generate the same effect, because it’s all presented in one “voice.” Maybe a really talented voice-actor or monologist would be able to mimic the effect, but in general, a series of quick descriptions presented by the GM will feel like a single long “shot” more than a montage.
And that realization–that Painting the Scene basically mimics the effect of a montage–points at the best times to use Painting the Scene. It’s going to work best in the same sort of moments that a montage works in film: to establish a new scene; to transition between scenes in a way that implies considerable distance in time/place; to gloss over “downtime” or “preparation” or “training;” to show epilogues, etc.
I guess you don’t have to use the Paint the Scene technique specifically, but any technique that rotates through quick contributions from each player will have some of the feel of a montage.