I went to Noisebridge and spend too long modelling and trying to 3D print the pick shape I wanted before realizing none of the printers here had the resolution for the small part I needed.

I then went to the laser cutter, cut out a few circles, and sanded the edges to get the rough shape I was looking for. 

The same problems remained, which make sense because the sloping part of the pick only take effect on the last few mm of the pick itself.

I then tried cutting circles in some thing acryllic to see if the pick would bend to create a strumming-like effect. The acryllic was still to stiff to help.

The problem is much more prevalent on the back swing, because it's not actually the strength of the solenoid but the strength of the spring that is pushing it back.

Next tests will include: Trying a flimsier material for the picks, trying a fully circular pick, and trying a stronger return spring. The issues with finding a return spring with the right chance is the only store I've found with the specs I need is thespringstore.com, and they have a $40 min order. I'd rather not drop that much money on a few test springs.