The way Dale describes his working practices feels contradictory. He addresses loneliness by saying he goes out to coffee shops and bars. While that may be nice for Dale it wouldn't enfuse me with confidence (were I his boss) that he is focussed on MY needs. He says that it is very important that a remote worker is open to as many communications channels as possible. But he doesn't start work until late morning and then works through into the night. If his colleagues need to speak to him at 0900 where are the communication channels into his dream cycle? If he needs to talk to them at 2100 does he call them at home when their working day is done?
My gut feeling is that this works nicely for Dale but not so much for his colleagues!
Actually it worked well when Dale and I worked together. Most comms are near-real time: e-mail to the mailing list. For 'now' real-time you have chat, and for 'actually now, really now' you get on the mobile phone. My working hours were typically 7am to about 4pm and then again 9pm til midnight so we got good overlap.
As his boss, addressing his loneliness and isolation was one of MY needs - people's performance isn't in isolation of the rest of their life. For Dale this never turned out to be a problem, for others not so...
My gut feeling is that this works nicely for Dale but not so much for his colleagues!