That playfield looks in great condition.

I've never played a really old game like this, just looking at the flipper configuration how difficult is a game like this to play?  Seems like it would be damn hard just keeping the ball in play and getting a flipper onto it?

Playfield has some slight planking.. the white you see is mould!

Woodrails are a different game to play.. you have to remember that flippers didn't come into play until 1947.. this is 8 years after that and although their game play was firmly entrenched by then, many flipperless qualities are still present.
The wide space between them you just would not see these days.. in fact with BTDK im sure that its impossible for the ball to pass between them ( I walked away from a game on this). In many woodrail game strategies, losing the ball can be as important as keeping it.. often its impossible to get a fundamental feature without losing the ball in the right slot.
With this game.. the ball travels down to the 2" flippers.. you don't time it right ( timing is crucial on 2" flippers) and the ball slides to the centre outlanes. Now a modern pinball player would groan and watch the ball go between one of them and rack up a bit more score... a woodrail player would give the machine a bloody good nudge to possibly bounce it off and back onto the flipper for a second chance.. a woodrail player would be nudging the machine to get it into the correct roll over at the top of the PF.. they would also be keeping that ball in between the top 2 white bumpers and the red bumper for as long as possible.
Nudging the machine to maximise every opportunity but just falling short of TILT is all part of a woodrail experience.. these games were designed to  have body play.. the legs flex a little etc.. body is as important as flipper fingers.
If you ever get the chance to play one.. then don't be shy, they require a bit of nudging..