Afraid I can't help with drawings, but on the first point I think you are worrying unnecessarily. The oil will soon purge the pipe by merely pushing the air into the steam-chest.
Assuming normal practice, in which the oil-pipe is connected to the steam-circuit simply by a union nipple:
I think you will find a test-point as you suggest will not really test anything because the pipe is open-ended either effectively to atmosphere when the engine is cold, or to steam in running conditions.
In normal service the lubricator soon reveals something is amiss by the oil-level not dropping; and I have never seen nor heard of anyone fitting a bleed-valve in the oil-line, in miniature or full-size.
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Under running conditions a bleed-valve between pump and valve-chest will simply emit a lot of steam. A pressure-gauge there would show a pressure – but of what? Oil or steam? Or some resultant pressure? It will not show oil is actually being delivered to the steam circuit, though a blockage downstream might create an oil pressure above boiler pressure.
Used cold, and turning the lubricator manually, the bleed-valve will emit some oil, but most of the oil will take the easier exit, into the steam-chest. A gauge will show if the pump can give adequate pressure only if the pipe's outlet is plugged, or the gauge is connected to the pump directly – i.e. no outlet for the oil.
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So where does this leave us wanting to test the mechanical lubricator?
In service: A mechanical-lubricator is self-purging, and shows it is working by the oil-level falling. And by very oily soot in the chimney top if set to be a bit too generous – at least erring on the safe side.
Cold: The lubricator can be tested new, after a service or if suspect, for flow by an open outlet, and for pressure, by direct connection to a pressure gauge; and manual rotation.
The oil-line including any in-line check-valve can be tested (I have known them become blocked) only with the engine cold; by disconnecting the delivery end and again, operating the pump manually.