I think the bar is raised much higher for telecommuting, because of the need for trust - a virtue not normally associated with successful businesses.

I've had several jobs where I started off working in the office, and when negotiating contract renewal after an initial six months was able to get telecommuting considered as part of the package. I think that the initial period was important for several reasons: on the one hand to show that I was inclined to work all the hours I billed, that I tended to complete projects within time and budget, that the finished code was usually easy to deploy and rarely caused later problems due to bugs or to grey areas in the specification; and on the other hand to get an understanding of the day to day business of the company and of my colleagues - what sort of people they were, their strengths and weaknesses, and how to communicate with them.

The only job I've had in which I worked at home from the start is my current one, and there I had the advantage of word of mouth: the director of technology is someone I've worked with several times in the past (indeed I gave him some initial perl lessons, way back when) and a close personal friend. And in this job, more than in any previous one, I feel occasionally isolated from the rest of the team, and more likely to have problems with communication, because I have never worked with them cheek by jowl and learnt their peccadillos (and given them a chance to learn mine).

As far as applying for jobs is concerned, I would never send a CV in isolation: I'd always contact the company or recruiters directly first (by phone if at all possible) to ask some more details and warn them my CV was on the way, and then follow up with regular additional calls to check that they had received it and find out what else was happening. Indeed, many of the contracts I've taken were not what I originally contacted a recruiter to apply for but arose thereafter because I kept in touch with them. Don't get me wrong, most recruiters in IT are quite terrible, and will try to push you in inappropriate directions unless you are firm with them (to the extent of modifying your CV to be a complete lie without informing you), but I've found them to be a necessary (or at least useful) evil.

Hope some of that helps,