I am not even sure that will work. Usually VPNs will use UDP for performance reasons. Tor is essentially a SOCKS proxy. While SOCKS5 in theory supports UDP, in practice it is quite problematic and not a lot of server implementations support it. So you would have to use TCP for the VPN connection, which has a whole slew of different issues.
Given that you need to pay for the VPN, having your connections exit at the VPN, may expose you more than the other way around. It all depends on whether the VPN company logs or not.
Thanks a lot for your contribution in this thread. It was really appreciated.Also as a personal note: While I greatly appreciate all the questions, I will ask to have this thread closed on Monday. That means you have around two more days to get your questions in.
This probably won't be the last AMA I will do. Since you guys enjoyed it quite a bit, we are thinking of doing an AMA on a semi-regular basis and open it up to more communities and social media. So if you missed this one, you will definitely get another chance in the future.
Yes, in theory you should use your VPN in TCP mode. The idea is that, using this configuration, the VPN provider would only have your TOR ip address. So that's why I thought it was great from an anonimity standpoint. However, in theory it's quite difficult to setup and speeds are really low