EXPERT RESPONSE
I've been reviewing this question for a few days now and think the best
answer for your question is to provide standard best practices for all
applications using a VPN and SSL. The VPN will provide packet protection for encrypting the packet and headers. SSL will further protect the data. The VPN will wrap the data packet and provide point-to-point (user to company) protection, while the SSL will provide end-point to end-point proof
of protection.
Your question is rather complex and requires many more questions and answers,
but I think the answer above should lead you on the correct path.
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