If the first thing is to put the trans into "N", the risk of still being on the throttle when you do that is greater and one has to figure car speed also. My situation was/is different because I had a hand brake instead of a foot brake so the right hand was really busy.
There is enough oil remaining in the galleys and dripping from being slung around that for a few seconds without gauge pressure (and no load)is really not that big of a deal. Milodon pans are notorious for slosh problems, but never had a bearing issue because of it