Here’s my list (from left to right as they appear in my Dock):
Transmit – FTP program. Used to use Fetch, but Transmit is more intuitive and easier to use…even for an “expert” like me.

Direct Mail – Bulk Mailer program. I have a couple groups of 100 or so people that I email for events, etc. This program makes it easy to send out either text or HTML messages, directly or via SMTP.

Skype – Popular voice over IP app. Talk to anyone, anywhere in the world over a high speed internet connection, for FREE. Also available for PC.

TaskTime3 – Ever have troble keeping track of how much time you’re spending on a project? This little gem will put an end to that. Nice interface that lets you sort jobs by client. A real keeper.

Feeder – Just started doing a bit of Podcasting and this little guy makes writing the .xml file a piece of cake. For $29.95, I just couldn’t afford the time it would take to do it myself.

OmniGraffle – Nice app for creating flowcharts and diagrams. Pricey at $79.95, so more of a “business” application…which is what I use it for.

Renamer4Mac – Ever have a bunch of files that you want to rename in a sequential order…like some photos from a birthday party or something? It’ll never be any easier than this…can put in words, etc. i.e. jason_30th_birthday_001.jpg. Handy, huh? Donations accepted for this, but otherwise FREE.

Cocktail – Sounds like fun, huh? Well, sort of, but it will get rid of that hangover your Mac may come across every week or so—especially if you rarely restart your Mac (like me). Runs some scripts and fixes preferences and does some other tekkie things I really don’t understand, but bottom line, makes your Mac run like new. If you’ve got more than one Mac, get the Family Pack for $29.95.

SilverKeeper – No one can afford to lose all the data on their computer, so make sure you back up your system. Buy a LaCie Hard Drive ($150 for a decent size), and this little app is a FREEBIE. You can set it up to automatically back up your system every day, or you can click the big blue button on the interface and it will do it at your whim.

SnapzProX2 – Take screenshots. OK, I know you can do that without buying a program, but this app will let you select an area with a marquee, select a window to shoot, or even record a movie of a process taking place on your screen. One of the first Shareware’s I purchased for OS X.