When is the best time to incubate? When you can and it suits your schedule and conditions.
I always have a five-day trip in March. I usually put eggs in the incubator just before I leave for that trip. If I top the water reservoir off just before I leave it will be fine until I get back. But I will not have a hatch date anywhere close to that trip. I did that once with a broody and she hatched two days early. That messed up the girl taking care of the chickens when I was gone. So fit it around your personal schedule.
My brooder is in the coop and not in the house so I don’t have any pressure from my wife to get them out of the house. So what facilities you have for brooding them needs to be assessed.
Where is your brooder and how warm can you keep it? You don’t have to heat up the entire universe for them, just provide a warm place for them to return to when they get cold. In really cold weather it’s not a bad idea to warm up the area where the food and water is a bit but this area does not have to be anywhere near the 90 degrees the first week and drop it 5 degrees a week you often read about on this forum.
How often do you have power failures and such, especially from winter weather? They don’t necessarily need the 90 degrees the first week and drop it 5 degrees a week you often see on here, but the colder it is the more they rely on that heat.
Why are you hatching them? What pressure do you have to hatch them early? I normally hatch some in March because that’s about 4 months before the chicken in my freezer runs out and I’ll need to start processing some more. That’s a personal decision you’ll have to make.
I don’t have a clue when is the right time for you to start hatching. That has to be based on your unique conditions and goals. Hopefully this will give you a few things to consider. Good luck!