Blimey, this brings back utterly fantastic memories of CS. I could play for hours and hours and never get bored... Maybe I've grown up a little since then, but the whole community/scene just doesn't seem to be the same.
Joebob - A server with just the classic maps on sounds excellent. My only worry would be whether you could build and sustain it's popularity. These ideas always seem to start well, but you end up with a server that's empty most of the time. A lot of the maps mentioned are only really enjoyable when completely full in my oppinion. But if you could pull it off, I'd be a happy man!
Oxygene - Have you seen the cs_seige remake:
http://www.fpsbanana.com/maps/5660? You've got all sorts of classics on there which might be worth checking out before getting too far down the line.
as_oilring:
http://www.fpsbanana.com/maps/11636
cs_747:
http://www.fpsbanana.com/maps/10540
cs_arabstreets:
http://www.fpsbanana.com/maps/17593
cs_backalley:
http://www.fpsbanana.com/maps/5033
cs_estate:
http://www.fpsbanana.com/maps/12465
cs_thunder:
http://www.fpsbanana.com/maps/4479
de_survivor:
http://www.fpsbanana.com/maps/11765
de_torn:
http://www.fpsbanana.com/maps/12958
de_vertigo:
http://www.fpsbanana.com/maps/19118
There's a few which I'm unable to find (i.e. Vegas), but that might give you a platform to work on. I've no idea of the quality of them, but from the screenshots they don't seem too bad.
Also, along with Joebob, I'm more than welcome to assist on the web side of things if any further help is required.