OffWhine

Hello, i would like to achieve a high level of anonymity in web-based applications(mainly browser) and would like to get some input by experienced users! The Goal is to not be tracable(as good as this is possible) and to have encryption aswell. First i thought of chaining a list of Proxies(at best in a random order for each package sent)before entering an SSL encrypted VPN. Through that i hope to prevent danger from sniffing into my traffic from the proxies due the encryption of the vpn and the different routes through the proxies hide my Identity from the vpn. Does this work? I am not sure how a SSL Handshake will hold on this(what if the last proxy is always the same?). Additionally i would like to add another Transport Layer Encryption (SSL proxy?, second VPN?) to prevent spying my data by a possible corrupt vpn. I find a lot of information for each topic itself but im very unsure if my idea works in generell, or which tools i can use for this. I have advanced Java, C#, and Web-development knowledge and would like to expand my very basic linux ,bash and network skills. Im also willing to try myself on c for this project, if necessary as a long term target. Please just share some links thoughts and input for this idea!