So, after all this work trying to figure out how to do this using masks, filters, etc... the solution was actually dead simple.
I ended up just placing the main image over top of a taller transparent image (at the correct distance down from the top to create the perspective), then applying the plane2cylindar to that whole image.
So crazy I didn't see that to start. Thanks for the thoughts and help though.
Edit - more details on how to achieve this.

$finalimage = new Imagick ('flowers_with_perspective.jpg'); // The final image
// a canvas with no background that sets the foundation for the perspective I want.
$canvas = new Imagick ();
$canvas ->newImage ($width, $height+200, 'none'); // $height should be the input file size plus a bunch of extra height (200px for example).
// the image I am want in perspective (the flowers in my example)
$image = new Imagick ('flowers.jpg');
$image->setImageBackgroundColor(new \ImagickPixel('transparent'));
$image->setImageVirtualPixelMethod(Imagick::VIRTUALPIXELMETHOD_TRANSPARENT); // make sure it's in transparent mode so when I overlay it on another image it doesn't have an odd background
// get vertical offset for $image on $canvans
$top = (($canvas->getImageHeight() - $image->getImageHeight())/2) +100; // should offset flower image 100px down from center
// apply $image to $canvas at 0px left and $top px down from top
$canvas->compositeImage ($image, Imagick::COMPOSITE_DEFAULT, 0, $top);
// at this point we just have the normal 'flowers.jpg' but displayed 100px down from center on a larger, transparent canvas.
// now apply plane2cylendar to create perspective on entire image
$canvas->distortImage(\Imagick::DISTORTION_PLANE2CYLINDER, [26], true);
// now you would apply the canvas to $finalimage along with other filters/overlays/etc you'd need and save!