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Snaggy is a web-based tool for drawing on, annotating, and sharing screen captures. To draw or write on your screen capture just paste your screen capture image into Snaggy. Snaggy offers tools for highlighting a section of your screen capture, typing on it, and drawing free-hand on your image. You can also use Snaggy to crop your image. When you're ready to share your screen capture, Snaggy assigns is a custom url that you can Tweet, email, or post anywhere you like. Snaggy lets you save your edited screen captures to your computer too.

Great open source drawing program for most OS platforms. Well recommended by my Twitter PLN.

Great tool that lets you draw on your webpages - insert text comments & arrows - and you can publish the pages if you like. Nice freeware app. Simply drag an icon to the bookmark's toolbar.

Snaplr is a simple way to capture and annotate your desktop's activity. Its Free to download. After taking your screenshot, you can highlight a specific screenshot area further with a set of drawing tools. Copy your screenshot to the clipboard and paste it to an email or save it as a png attachment instead.  Works great in Gmail and Outlook. I like using this in Windows as Google Chrome doesn't have the best screen capture extensions right now that can annotate as easily as this tool.

The two I'm especially interested in are BigMarker and JoinMe. JoinMe is a good way to share screens and to actually work on someone else's computer. BigMarker gives the ability to do voice/video conferencing. Richard Byrne suggests using it to provide online tutoring, brainstorming sessions, and other online presentations. You can have a public or private meeting room, can share screens, and it comes with a white board you & others can draw on. I saw something that indicated you could upload docs & share those, as well. Lots to consider trying.