I've done a few stints of 3 months nonstop on the road, and when I had an employer we typically had weekly & monthly milestones, and no Skype meetings. Our communication was asynchronous (email back then). They'd often ask for smaller things 'ASAP', but as long as everyone understands that could take up to 24hrs, it works fine.
[I would lean towards freelance & self-employment when doing this, though. My income was supplemented by products I sold myself online too.]
Not wasting 5-10 hours per week in rush hour traffic is a pretty big perk, even if the working hours are pretty much set.