I've raked 4 or 5 times. A lot easier to do a quick pickup (15 mins) than waiting until it becomes a big soggy wet mess that takes an hour and weighs a tonne.
That way you can just mow in-between and that becomes another pickup cycle, and your property is going to look tidier. Win/Win.
For anyone who does raking, I implore you to get these. It takes 3 or 4 grabs to fill a garbage bag, versus watching others do it handful by handful for an hour. Plus you can use it to re-collect leaves into a pile if they get scattered during pickup.