as a side note.
I dumped OSx and went ubuntu on it.
apt-get upgrade
much easier.
Reviving this but,
It sound pretty much like my set up:
local windoz -> local ubuntu ( testing) -> rest of the world servers
The last issue in your post was to ftp or to sftp between the 2 locals
I am using netbeans on windoz and I still have not been able to figure out the most chroot chown chmod combination so that what I upload to the ubuntu box is close to a live site.
I am assuming the followings:
/var/www/ nut:nut
/var/www/sites/ nut:www-data
/var/www/sites/nut.com/ www-data:www-data
Could you describe what it looks like today?