I want to create multiple bing/yahoo accounts, do i need a separate ip address for each? If so, anyone recommend a vpn or proxy?

I thin they track with javascript so I'm not sure an Ip changer would work. I would suggest going to the services offered section and just hiring an experienced person to do it. It will save you time and frustration.

I have multiple Yahoo accounts, funded by same CC, etc, and have had them for over a year with zero problems.

What? Funded with the same CC? You actually pay Yahoo for email accounts? Why?