Should the pin just barely touch the neck going in? Should it have more than just barely touching? I assume now it should have some contact with inside neck for determining proper ID to set all this up. Looking for how the pin should fit in the neck to determine it’s the proper size vs the next size down.
The step size of your pin set will limit your ability to get too fancy with this.
When your pins step in 0.0005" increments, your feel will be based on the quality of the brass and the defects in your necks.
When a pin slides straight in and doesn't feel tight, step up to the next one.
Never use a dry pin.
Be sure to leave the pin slightly lubricated with sizing lube to avoid sticking.
When the next pin up seems like it takes torque and force to push in and out, you have to use some judgement to establish your own standard for calling the size either the last pin you could push in without grunting, or the one before. It is arbitrary so just be consistent.
In industrial work, we have pin sets that step in 0.0001" increments. We also train the techs based on handing them blind tests of samples we have measured with much more sophisticated methods to give them a feel for the pins.
It is easy when the brass is virgin with good finish and geometry, but more difficult when it is rough and out of shape. The elasticity of the case neck is magic compared to many other challenges, but it takes some practice to get a technician "calibrated" with gage pins in different types of context and metals.
Don't let this scare you, just get rolling and be consistent, taking good notes. Don't call one while slipping the pin in and out loose like a trombone one day, and use lots of force the next. There would only be roughly 0.0005" difference between a loose pin and a pin that takes effort to slide in and out. With some practice, you will get the hang of this fast.
The challenge is to learn to detect chamfer, contamination, burrs, etc., and tell the difference between those and the actual ID. You are reloading used brass versus setting up a virgin production line, so you will detect powder residue and your chamfer workmanship and soon you will be able to tell the difference.
Practice on some virgin brass to get a better feel, then also try to gage some fired-unsized brass if you have the pin range.
Happy New Year!