The assembly and operating instructions leaflet that originally came with the HMV 102 gramophone was fairly brief on the actual use. It includes winding instructions and how to place a new needle, but funnily does not mention actually placing the needle on the record. By that time this would be common knowledge of course, so the oiling diagram is probably better use of the leaflet space.
On the entirely other end of the spectrum, a record sleeve for HMV classical records from the 1920-ies contains a most detailed description of how to play a record. (Dance records came with another sleeve text, on the marvels of creativity of the modern dance band.)
In detail; points to get the best results and properly play a record on the His Master's Voice gramophone.
About the pushing in; most records up to the thirties don't have a run-in spiral groove on the outer rim to 'catch' the needle when it is lowered on the outer rim. Most are just plain flat on the outer rim, so the needle can be pushed into the first groove. Some records have a thick ridge on the outer diameter, so the needle at least cannot drop off the record. This ridge seems to be mainly on older (before 1920) German-made records so far.
The run-out on early records is very varied. Some have no run-out at all and just stop, some have a very thick-ridged spiral to a smaller circular track or even just to pretty much launch the needle onto the label. Most do have some sort of spiral or oval to move towards the label quickly, so the auto-brake usually works on these.
Took a while for 'standard practice' to settle in. A fun area to discover :)