Working backward through you post, many of us bought our cars used, so first want to check that the fluid level is as specified.
Why so complicated? because as I mentioned, the push for lowest hood lines, lowest center of gravity, and with still-adequate ground clearance. Not so easy when Camrys and Accords fight for market share selling near-identical cars.
It would be simple to specify that the fluid be checked at the thermostatically-controlled normal operating temperature. But, because of the stand-pipe level check requiring that the technician get their hand bathed in transmission fluid, a temperature was chosen that was intended to allow a car's fluid level to be checked quickly, first thing in the morning, without cooking their fingers. No doubt that many cars leaving the service bay will have to have this done first thing in the morning, before customers start walking in to pick up their cars.
Also, I'm sure that it has been a regular problem for car makers and their dealers over the years having to deal with customers that have checked their own dipstick fluid level without using the prescribed procedure, leading to unwarranted complaints of "incorrect" fluid level.
Not to mention dealing with transmissions malfunctioning or damaged as a result of a customer not following correct procedures as to 1) engine running 2) level ground and 3) fully-warmed transmission fluid.
You can also be sure that these customers of the past who (with good intentions) still screwed up their transmission fluid level or added the wrong fluid (in an "emergency" of perception only) would often enough claim that they did nothing wrong, causing possible repair expenses that who-knows-who had to "eat".
So I think that "dipstick packaging" concerns likely were among the least of concerns leading to the popularity of "sealed for life" transmissions.