Before I've used Tor for bad intentions and because of curiousity on how does deepweb differ from what is filtered on the surface. I have seen much evil that im not gonna go back again. If you're in a country that restrict gambling online, I think vpn is enough that my friend does the same. Tor network won't insure anonymity or any kind of virtual private network won't help you hide your true identity if in your own your not careful with it. Bitcoin address is highly traceable and if without proper mixing of address and vpn it won't work. A simple mistake will trigger more damage that you won't know.
I've surfed deepweb once, there's nothing scary and to worry about, and ofcourse I always follow the guidance to make sure my safety, and holy shit, there's so many illegal porn content there people said but will never visit it though. and also, it seems that the deepweb itself is just bunch of people who want to try something different, nothing as scary as what people said.
and one thing, what's the deal of hackers knowing your address tho.