upgrading a production server

[John Dangler]

I currently have a production server running Breezy Badger (5.10) which
I keep updated.

My workstation and laptop was running Badger, and in order to get them
to run Dapper, I had to do a full install and manually set up the apps I
wanted on them since dist-upgrade was a dismal failure.

With Edgy just around the corner, I'd at least like to upgrade the
server to Dapper, if not edgy.  The server runs php5, mysql 4, apache 2,
bind9, qmail/vpopmail, iptables, clam, and supports our websites and a
few small company applications.

I'm really nervous about an upgrade since this server is my livelihood
as well as my testground.

Any insight or assistance is greatly appreciated.