Using a VPN and Tor together can actually make your privacy worse in some circumstances, not better. Your VPN server essentially becomes a fixed entry node or exit node to the Tor network, depending on whether you connect to the VPN first then Tor, or route through the Tor network to reach your VPN server.

Connecting to your VPN first and then to Tor will certainly hide the fact you are using Tor as we have discussed above, but the same is possible with pluggable transports. This set up is fine if you fully trust your VPN provider not to be keeping logs, but otherwise provides little benefit over Tor alone. Obviously you should still be using a VPN at all times whenever you connect to any public wifi.

Using Tor to reach your VPN server is a terrible idea and completely negates the entire point of Tor. You are giving a single entity (your VPN provider) access to all your traffic, which they could link back to you via traceable payment methods or previous IP addresses logged (if they keep logs) against your account.

Someone correct me if I'm wrong, but I can't see any benefit to using both a VPN and an obfsproxy bridge simultaneously to connect to Tor, unless for some reason you wanted to hide the fact you were using Tor from your VPN provider?