Joining two cutaways with fade while avoiding jump cut
I just migrated to new MB Pro and now using iMovie 10.0.6 from iMovie '09.
When editing together two or more cutaways (abutting), can we no longer use a fade without producing a jump cut?
For example, I'm laying multiple still shots of cover over someone talking. If I want the multiple shots of cover to fade in and out, even the slightest 0.1 second fade produces a jump in the transition back to the main video (a flash of the person talking). You could directly join cover shots in iMovie '09 but I can't figure out how in latest version. I've tried dragging the clips every which way (overlapping, atop, etc.) and doesn't seem any way to use a fade transition without a flash of the talking head (or main video), just a hard cut is the only possibility. I've tried everything. What am I missing?
Thanks.
MacBook Pro with Retina display, OS X Yosemite (10.10.1), iMovie 10.0.6