I hunt more than deer, e.g. ghogs, predators. Between hunting and practicing I shoot approx a thousand rounds of centerfire rifle a year out of 14 different rifles. I wanted a sizing process that would produce reliable chambering; every time for every rifle.
I don't like the idea of chambering live rounds at the loading table, i.e. in the house to see if they chamber. Don't much like the idea of having to take the bolt apart every reloading cycle either. The idea of checking each round would be tiresome*. Instead I opted for adusting the die so the bolt will close just as you suggested which the .001 to .002" shoulder bump process accomplishes without having to check each round. This way I know without any doubt that all my reloads function without any problems but I also haven't oversized the case to create excessive headspace.
As far as imagining a problem that doesn't exist, well it happened to me more than once in the field when I was a 'neck sizer' and I can assure you I wasn't imagining it. It's the main reason I switched back to full length resizing but learned from a benchrest shooter how to do it right by measuring the amount shoulder bump from a fire case in the specific rifle that I'm reloading for. It works quite well so "I'm not worried about functioning in the field" any more.
As far as how many cartridges I need to kill a deer, only one if I place the shot correctly. For ghogs and predators it depends on how many I see and get shots at. Also would hate to drive 15 miles to the range to practice and find out that some of my reloads won't chamber. It would upset my digestion.
* Being kind here, actually it would be stupid for the amount of rounds and number of rifles I shoot.