...what does it mean to you...?

I was surprised by one of the meanings.

That time when you would expect to see the most winter like weather for your specific location based on your past observations.

Do I win anything?

Pretty much the same as "dog days of summer"

Not much happening.

When the last new Forensic Files show runs for the season

here its the "mud of winter"

Probably not every year

Sorry gray dog, no prize except to pass some time in the "dead of winter"!

To me, its always meant some place in the middle of winter where a person can be tired of it but there's more winter left. Thus, if you chop up the actual months it would be somewhere in the middle-to-end of January. But then I read this definition that links the darkest part of the year and it doesn't strike me as the dead of winter around Dec 21 for the northern hemisphere but I suppose it depends on your latitude as well. January is usually the coldest month of the year yet light is coming back by the end of the month even if cold and snow remain.

https://www.bloomsbury-international.com/student-ezone/idiom-of-the-week/1702-in-the-dead-of-winter/

Your source is Quality English Scool in Central London. Dead of winter isn't so bad if you've got a bedroom skylight, a crystal clear cold night, the northern lights overhead, a bottle of wine, and a heating pad to provide relief to your aching body. Granted it could be better.

It means right now.

That sounds pretty good but I would prefer a good rye whiskey instead of the wine. Maybe I'll put a skylight with northern lights and a warm bed on my bucket list...

Whiskey causes an allergic reaction. Found that out years ago.

Here its all the time after August and before May.

Dead of night Dead of winter. Well into it and a long way to go get out of it

That's still one of my pick up lines. I walk up to a lady, nay, I swagger up to a Lady. I look her in the eye and say, Baby, you lookin better then a new set of snow tires in the dead of winter, you wanna dance. Yeah, that's how I roll.

yeeah buddy.

Right in the middle of winter.

gives "talk to the hand" new meaning.

I always thought it was the exact middle. Just like dead of night. I believe they both come from the "dead" center of a spinning object as it doesn't move. A term used on lathes. Or my other thought was the center of a target. You hit the center and the target is dead.

I'll take the dead of winter over the dead of summer.

Exactly...almost feeling it.