I came up with a way that works better than my molded ear. Just requires some tubing, e6000 glue and hot glue.
Various vinyl tubing and one latex for the connection to the mic.
Staggered them to make a 'bowl' like area. Filled in with e6000 glue. Still wet in this picture and needed a second layer.
Cut the largest diameter tubing into a 3 prong claw or crown shape. Roughed up the inside of the tubing with a razor blade at the tips (for better adhesion) and applied hot glue.
The crown or claw can slide up and down the inner core to change fit depending on earbud shape. The arms flex and fold so earbuds can be inserted, positioned and removed relatively easily. I'm able to take repeatable measurements fairly easily, still some finickiness but not bad at all.
Here's some comparisons of the two different couplers I made. It is easier to get repeat results with the claw/crown style. It also seems to catch upper mids & especially treble better.
These are the measurements that seem mostly the same. There were several that were massively different (mostly in the bass & lower mids) depending on fit until I figured out what positions worked best.