I've been working remotely for the last decade in various forms (first as a salaried employee and now as a consultant) and my thought has always been that you really need the same drive and self-discipline to remote work as you do to start your own company.
I have my own office, but I can also work from pretty much anywhere that has an Internet connection.
A few years back, I worked worked on an all-remote team that had a high turn-over rate. The reason was because nearly all of the new developers that were hired would work fairy well for a couple of weeks..and then productivity would drop off to nothing, meetings would be missed, and communication would be sparse. Management didn't really know how to weed out people that most likely wouldn't work out.
On the other side, I had a project manager at one of my more recent contracting gigs that didn't know how to effectively communicate. I tried many times to foster communication and the end result would always be the same: missing task/project requirements. This rarely happened to me before this point in my career (if it did, it was addressed and quickly fixed) and it was happening more than half time time and the project manager was unwilling to change.
The company eventually ran out of funding before I quit (and still hasn't launched their service 10+ months later).
The challenge with remote employees is that you not only need a good employee fit, but a good manger fit.
Remote working is quite new to us though. People have worked on site for thousands of years, while remote working just appeared in the last century or so and it has different communication needs.
My guess it will take 10+ years from now to cultivate remote communication skills so that they work intuitively for the majority of software developers.
