I used to run a 50L keggle double batch system, with a pre boil of about 43L (as close to full as comfortable) and knockout of 37L. I've done it a number of ways. As below in order of preferrence;
1 - 37L post boil with 8L top up in kettle into 2 x 20L cubes (3L kettle loss)
The top up water when added to the kettle at flameout helps to rinse the trub of sugaz... at least that's my theory anyway. I thought i read something about it around here, but buggered if i could find it.
2 - 37L post boil into 2 x 17L ex fresh wort kit cubes with 8L top up into fermentor (3L kettle loss)
Most commonly did this as I just had the 17L cubes at hand. It was also convenient to add boiling water to fermentor as a sanatising step, let cool then pour in cubes.
3 - 37L post boil into 2 x 17L ex fresh wort kit cubes. (3L kettle loss) Fermented at gravity with 8L top up into kegs
Did this a few times... didn't like the results. Beer has finished fermenting at 1010-1012 or whatever and i come along and dilute it down some more, thereby taking a point or to off FG. Came out a bit watery.
No reason any of the above methods wouldn't work if chilling i guess.
Now have an 80L kettle and it's set and forget with a very comfortable pre-boil of 51L for 43L knockout and 38L into kegs.