There's a chap called Roger Davis (I think) who is a singer from Huddersfield who I saw doing a fair share of playing a few songs at singarounds and he progressed to playing at all sorts of things. Stan Graham I think started at local places and has since toured to New Zealand with Vin Garbutt who also recorded one of his songs. Hissyfit started singing in local places and have progressed on to playing at Perthshire Amber, festivals etc (I think we gave them their first paid gig at our local pub!) David Swann plays everywhere in Yorkshire some free some not. Wendy Arrowsmith (who might chip in if she weren't on holiday) would probably be able to give you lots of advice and she is now establishing herself at folk clubs around the country.

Most of them still do a fair amount of singing in very informal free singarounds etc becaus ethey dearly love singing and playing

So it is both possible. It depends what you want.

I even remember, I think, one of the Unthanks singing in our local pub the best part of 9 years ago in an interval when Last Night's Fun came and played to an incredibly small but very appreciative crowd.

I think it's what used to be called 'paying your dues'. My son is doing the same playing electric guitar down in London which is equally hard!