I've been a remote worker for maybe 5y now. I realise now that I've spent more time working remotely than I have in an office. My experience with getting hired on various jobs has been: the people with who(m?) I've worked remotely with before (for example, because they've been somewhere else at a different organisation) have absolutely no problem (and are enthusiastic even) about hiring me, and the people who have not interacted with me in that way, and especially not worked with remote workers before are really very wary indeed - but the enthusiasm of the people who have worked with me remotely is enough to overcome that. There's clearly a division, and clearly people can move from one side to the other, but it seems very individual: people are happy for me to work remotely rather than for "staff in general" to work remotely. So there's a reputation thing going on - but it doesn't seem a reputation that is widely understood - its a reputation understood only by a set of people who've had the experience. I don't really know how that reputation can be propagated and understood by others without the hard sell from someone already in there...