So, how does the average reloader know how much to size bottleneck cases?
Back in the days before I had gages, I set up my dies by removing the cocking mechanism, extractors, from the associated rifle. I then sized the case, closed the bolt on it, if there was resistance, I lowered the die a bit more. That was how you did it.
How can one accurately know how much to bump the shoulders, if at all?
You can't measure tenth of an inch when your only gages are cubits and finger joints.
When I finally got Wilson type gages and went and measured cases I had sized, according to the technique in the last paragraph, cartridge headspace was all over the place.
My M1917 270, the receiver seats and bolt lugs are tapered so the bolt keeps camming all the way down. My 270 cases were all off. My 7.5 Swiss, it was very bad. That straight pull mechanism with all the cams and leverages working through a 8 inch (guess) long bolt mechanism, I don't know what I was feeling, but the cases were all way off. My 375 H&H belted magnum, I did not want to remove the bolt face ejector or the spring loaded extractor. When I got one of those Sinclair special gages, all cases were way off. Way, way off.
See the problem in using even a stripped bolt is that the bolt handle leverages and cam angles, bolt binding, and god knows what else that is in the system, totally ruin any sensitivity to bolt closure.
Another issue is that brass cases are springy and don't all retract the same amount. Brass from different manufacturers is of different annealing and work hardening, and they all come out of the die a little different length. That is why I usually have a case gage on the bench, I check the current brass being sized, and often, more often than I like, I have to adjust the die up or down a little bit because this brass is springing back a bit more or less than that last set.
Can this be done without all the fancy gauges and such?
It all depends on how much you need to control the cartridge case headspace. When shooting rapid fire, I want my bolt gun bolt to close without any extra resistance. It knocks me out of position to have to wrestle a bolt down. It is not worth driving two hours, a match fee, and spending all day at a match, just to have my score ruined by sloppy ammunition. I also don't want any jams or safety issues with Garands and M1a's.
People who just shoot on a bench, I don't think it makes any difference in anything if they have to get a rubber mallet and beat the bolt handle closed, or open.