Despite the newish version number, you may have first heard of Skitch years ago—it debuted as a beta at the 2007 Macworld Expo, making for a beta period that was Google-esque in its duration. But Skitch has come a long way since then, and the wait was worth it.

Skitch is a combination of an application and and online service that became integral to both my work and personal toolsets almost instantly, despite—or, perhaps, because of—its wild departure from the Mac OS’s core interface conventions. Whether I need to share a quick screenshot with a vendor's tech-support rep, crop a photo for a Macworld story, or make a lame attempt at a Cheezburger submission, I've found Skitch to be perhaps the fastest and most frictionless way to capture, annotate, and share photos and screenshots.

Bring up Skitch’s window and you get what is essentially an image canvas wrapped with a tool-filled border. The approach feels both creative and disorienting, as Skitch works in a number of mysterious, but ultimately successful, ways. Keyboard shortcuts abound, as do menu options for snapping a portion of your screen, a specific window, the whole enchilada, or Skitch itself. You can even pull images from Mac OS X’s built-in media viewer, which provides easy access to your iPhoto and Aperture libraries without having to open the respective apps. Once you have your image, a well-rounded array of annotation tools allows you to highlight important elements or, say, to put words into your cat’s mouth for the Internet’s delight.

Editing, saving, and sharing images are where Skitch gets really interesting. In most image-editing programs, cropping or resizing an image usually involves clunky dialogs or, if you’re lucky, a dedicated tool. Skitch takes a refreshingly straightforward approach: You just drag the corner of your canvas to crop, or the corner of Skitch’s window to resize—your changes are made on the fly, as you drag. If you need to create an image with a specific size (say, to fit your blog’s template or an editor’s requirements), a real-time dimension display makes it easy to hit those marks.

When it’s time to save or share your images, Skitch offers plenty of options. However, I’m not hip on the fact that the company requires you to sign up for a (free) Skitch.com account, even to save your images locally. On the other hand, the base version of Skitch is free, so that may be a small price to pay.

If you just want to save an image to your desktop or iPhoto, you click the big “Drag Me” tab at the bottom of the window and drag the edited image to the desired location or program—there's no cumbersome Save As dialog required (although you can still use one of those if that’s how you prefer to work). This makes it easy to drop images into chats or onto Upload buttons in Safari, or to import them into iPhoto. It also reduces the clutter of images piling up on your desktop.

If the Web is the final destination if your image, Skitch also has you covered. In addition to the Skitch.com Website (more on that below), Skitch supports uploading to Flickr, MobileMe, FTP/SFTP, and WebDAV, so you have your choice of free, paid, hosted, and your own services for sharing your images. You also get control over privacy at sites that offer it (namely, Flickr and Skitch), so you can, for example, add some images to a private set at Skitch and others to your public stream.

Once your image is uploaded to a service, you can post a link on Twitter right from within Skitch. The Skitch.com site offers additional links for sending to Facebook or Evernote, and even for copying HTML-formatted code for your own Website or blog. Uploading to Skitch.com also offers a number of benefits over other photo-sharing services, including the capability to follow the image postings of your friends, and to share your images with direct links or Web-forum-friendly code.

The company also offers a yearly Skitch Plus subscription for $20. This fee unlocks a few extra perks in both the application and the Web service, including unlimited sets for organizing your images; SSL security when uploading; support for additional image formats, such as TIFF and PDF; more editing tools, such as cropping templates for quick access to frequently used dimensions; custom font options; watermarking; and capturing entire Web pages in a single image.

I’ve found the new social features of Skitch.com to be hit and miss. On the one hand, while I use the app on a daily basis for both business and pleasure, I use Skitch.com to share mainly throw-away images for, say, customer service. (My "real" photos are all on Flickr and MobileMe.) However, Skitch.com could provide quite a bit of utility for design-team collaboration or even friends who want Tumblr-like image posting and a dedicated Mac app. In that context, Skitch becomes a drop-dead-simple blogging client that integrates well with other apps and the rest of the Mac OS.

That Skitch has both free and paid versions means you've got nothing to lose by just trying it out. The paid features and yearly price are quite reasonable, but the subscription model the company uses to unlock premium features in both the app and the Website—the latter of which many users may never touch—might put off some customers. Still, Skitch is one of those rare apps that took some risks to fill a useful niche—and emerged triumphantly.