Before you guys rip me to shreds, yes I know it is stupid. I should be using public wifi and all that jazz I know. I have some honest questions about it though. So I don't know if they do this all across the US but all the schools in the west coast that I've been to run it the same way as my school. In order to get onto the Wifi you have to go to a website, log in with your school account, then register your computer (or playstation or smartTV) with it's mac address, then you gain access to wifi and ethernet. Normal for a purchase I go to a random free wifi location, boot up tails, and run tor to my preferred DNM (Blackbank for the curious). However, I am on campus almost all day, and for simply browsing the DNMs I don't want to have to go to Mickey Ds everytime. So here are my questions 1. I shouldn't use tails correct? I assume that I would be unable to connect to the Wifi without registering mac address for tails, which would compromise my identity. 2. Is it safe to use Windows, with a trusted VPN, then tor? I understand this is less secure, however if for some reason they looked into it since I am running a VPN they wouldn't even see that I am using tor correct? Since it is my normal use computer do I have to worry about my IP leaking from some background program?
Sidenote, no I'm not freaking out over a gram of pot getting sent to me, it would be quite a bit worse if I got caught, which is why I am double checking my options.
Using Windows with Tor Browser Bundle through a VPN is a good idea in your situation. Just make sure that your DNS doesn't leak.