1) If they are pretty much guaranteed to work in the context of ICO's
2) Which specific VPN's have been used successfully in the past for participating in ICO's
3) Are there legal ramifications of using VPN's to participate in ICO's
4) What are the odds of being caught using VPN's to participate in ICO's
They are pretty much guaranteed to work. At this point, the most you'd see is simple IP restriction. A VPN should do, and for this, just about any VPN will work. If you are concerned about your privacy, use a no-log VPN like Private Internet Access. The legal ramifications are probably limited to not being able to seek legal recourse against ICO organizers (which you probably couldn't do anyway). The odds of being caught are low. As someone above said, just use a solid VPN and avoid TOR.
Awesome thank you for your feedback
Im just wondering if there's a chance that in addition to testing my IP address for not being from the US, that they would do additional forms of KYC like government-issued ID or passport, which would essentially foil my plans altogether
Or is it more like mutually-exclusive as in either they do IP address screening OR KYC ID/passport?
Therefore, many ICO teams require you to provide KYC information, only some of the ICO team allow you to use non-us IP for investment.