I can SSH tunnel using PuTTy as my socks5 proxy in my browser after I connect to my VPN or TOR and my IP connection showing up on my domain is that of my VPN.

If you set up the proxy first, then start TOR or the VPN, your connection will be your home IP to the Proxy first rather than the latter.

To answer the ops question though, yes, you can do a socks proxy through TOR which makes you look like your IP to the Proxy is from TOR and not your home IP(so long as the app you are using can do socks5, ie: browser proxy settings) -and- as long as the connection is made after TOR is started. If you own your own domain though, once on TOR, you can then SSH tunnel to your domain over TOR, but then your still using something tied to you, such as your own domain as your exit point and from there, no end to end encryption, but the same could be said for TOR since once you leave your exit node, the traffic between it and the destination you request is not protected unless also SSL or such. Not sure about all of that if using a public socks proxy through TOR, the proxy would become your exit point I would think and have control over what is sent back to you, including stripping SSL but serving you their own certificate 'proxied' version while being able to inject into what they send back or track, sniff, etc. Tor knows your original IP, but not who you were talking to or what you were saying.

If the target website uses SSL/TLS then the open proxy knows neither your original IP address nor the contents of your communication. Tor sees that you're making an encrypted connection to an open proxy, the open proxy sees that someone on the Tor network is visiting the target website. Going through Tor does allow you to hide your originating IP address from the open proxy.

Can you use tails as a tor proxy