For the most part, I change up my bags daily and keep my stuff in pouches for easy transfer.
Sometimes, I'll change my bags several times a day, depending on where I'm going or the weather.
When it's a new bag, I'll wear it for several weeks, maybe changing out with others bags every other day.
When I travel on business, then I'll stick with one or two bags for simplicity's sake and my Longchamp LPs as my travel bags.