So do you want an actual official winter break where the league is shut down in advance, or just an early start/late finish by a couple of weeks?
If we started two weeks earlier, played twice a week for at least the first seven weeks, and only scheduled one game a week from December to February INCLUDING CUP TIES, we should have the contingency to fit in all the postponements before the end of May. The League season would potentially be a third over by the end of September, though we would need to cut out pre-season friendlies almost completely, and Cup replays would not cause quite the problem that they currently do for some clubs.
It would mean playing Boxing Day/New Year's Day, but not the Saturdays of that week. And the Cheshire Senior Cup should be abolished.
A ten month season......but what would the players think of it ?