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If you do your residency on a J1 and return for two years to your home country after residency, how hard is it to obtain a working visa or PR in the US after the two years?
I don't really know. You don't get any preference. You'd have to get an H1b sponsored by your employer, I would think (although that might depend on what country you're coming from).
If your plan is to stay long term in the US, better to get a J waiver position. That switches your J to an H, and then you can apply for PR (after the waiver commitment)