>What are the HR roadblocks/hurdles that I would face in trying to get this candidate hired?
Most of the roadblocks would be in the form of communication and getting things done. However, if the person is capable of managing him/herself well and they are productive at work, whether in an office or not, the work will still get done.
>Could this person be hired as a contractor internationally?
That is what will be done. They will lose out on US-only benefits, but I've seen SV/SF salaries, and if you're paying that much to a person in a third-world country, they won't care for 401k or dental insurance. You should consult a lawyer for the best way around this (maybe a tax benefit too).
>If we wanted to hire them full-time, permanent would that require setting up an entity in the country that they live in?
Multinationals do this for tax and other benefits. You don't need to do this (unless you are producing a tangible product and there is big demand in the foreign market).