US startup hiring abroad – best/good practices?

We're a US domiciled startup and thinking about how to design comp pages, understand regulatory issues, etc....

For instance maybe it's easiest in Canada to have the person as a contractor, paying comp to an entity he/she controls. What to do about (say) health insurance they don't receive or lack of easy way to offer benefits (pre-tax commuter discount and other things PEOs in the US offer). I've read about Automattic but interested in resources/firms that help facilitate. (Using Canada only as an example)