Cms?
 

When would be a good time to start using one, IE: straight away or when you have half a dozen sites.

I suppose it would be a pain if you had half a dozen sites all set up and running and then tried to set up a CMS, not even sure if you could.

Are they really worth the money or is better to save money and just spend a little bit more time doing it manually.

I've always done things manually that's why a wanking machine doesn't interest me :1orglaugh

Its always best to start right away. Although some products, like CARMA, allow you to easily add content already on the server to the CMS and thus you can move sites to it one by one...

http://www.toomuchmedia.com/products/carma/

But it obviously is always better to start with one right away.

CARMA is only $150 per month btw.