Just laced up a fresh pair of Crockett 2's this past Sunday. My last pair of shoes (Brad Cromer's second pro Huf shoe, which I've had for like 4 years lol) still had some life in them after two months of skating 4-5 times per week for multiple hours each session. I flip my board a lot too and skate switch so both shoes get pretty equal wear. The sole wasn't completely bald, but I could feel my foot slipping when I pushed. I hadn't ripped thru the leather upper yet either, but toes were really worn down from flicking and the sides were developing a small hole. Probably could've gotten another week or two out of them, but it was time to move on. My board was toast and the shoes were about done too so I called it and set up a new board/new shoes combo. The Vans are taking a little longer to break in than I'd like, but once they do the shoes skate great.
So about two months lol.