Inc magazine had an article a while ago about working remotely (http://www.inc.com/magazine/20100401/the-case-and-the-plan-f...). Thought it was interesting. I'm curious as to whether or not more people are starting new jobs exclusively as a remote employee.
I've never had a professional full time job, as I started working for myself straight out of grad school. I have had numerous retail jobs that I had as a teen and during college, but that's a different story. So i'm not sure about 'how to begin that arrangement.'
My first job was as a one-man team managing a webapp for a local insurance adjusting company. I lucked into working remotely, as they didn't have a central office, so working from home was required.
My second job was working for AOL/Netscape under Jason Calacanis, and due to his experience with hiring remote employees for Weblogs, Inc., the idea of working remotely was not foreign to him or his other employees, who all worked remotely as well.
The same situation applied to my third job - Mahalo, working for Jason again, although since I left there a few years ago, they've transitioned to having all of the developers work on-site.
Now I'm back at AOL again, hired by someone I worked with the last time around, who himself was working remotely in the Orlando area until AOL opened an office there.
At this point, the ability to work from home is #1 or #2 on my list of qualifications for a job - I gain all of the time that would be lost commuting, my job market is much bigger than people who have to work on-site, and I greatly enjoy working in the office that I custom-built for myself (seend here http://news.ycombinator.com/item?id=2146210).
Most likely you won't start 100%, or even be able to get 100%. Get one or two days in the middle of the week to avoid the impression you're trying to get long weekends. Promote the extra time from not commuting, energy/green savings, etc.. There are lots of suggestions out there on convincing your boss.
Finally, remember that it doesn't work well for everyone. Some people don't self-direct well without the office environment, miss the social aspect and so forth.
My two dogs keep me company and when I need a break I can just go outside and throw the tennis ball with them in the backyard, no more spending my breaks still thinking about a problem. Huge collection of music to keep me happy. Plus I now have a corner office with plenty of sunlight.
I chose to do this for lifestyle reasons, to spend more time with the family and to be able to do my own thing at my own pace, without employees (strength peaking upto 50) harassing me :-) with issues every now and then.
Has worked extremely well for me; no complaints.
This comic pretty well sums it up how it's gone: