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Not to take away from the OP but you can enable a new feature in DropBox where screenshots are immediately moved to your DropBox directory, uploaded, and a share URL is stuffed in your clipboard. A notice is given on screen and on Mac OS X you get a notification center alert. I think I also hooked it into growl.

The screenshot is only moved, not deleted. It's in the DropBox preferences — and along with this feature you enable photo syncing and all your phone taken pics get put in your DropBox folder in "Camera Uploads", or the "Screen Shots" directory. You also get a good deal of bonus space for enabling these features.

You won't have time to grab the screenshot and edit it or draw on it. It happens fast. I use Skitch, which is a screen shot collaboration and editing tool. Once done, you can drag and drop the image to DropBox and get a share URL. Or drag and drop out of any app onto "Droppings", a small "app" I wrote.

I wrote a small script that fishes out your DropBox ID, which is used as your ID in a URL ( this is done once on install ). On receipt of a resource, the script creates a directory and time stamps it. This script is wrapped up in an app that accepts drag and drop. Drop a batch of jpg and gif etc., images, and it will copy them to the DropBox public folder, and put unique URL's to imgur on your clipboard. Full support for maintaining Mac Resource forks and all that as long as you compress on the Mac.

Drag and drop a zipped or compressed set of files, and it will do it's best to look and see if they are all web displayable, extract them, and give you a set of public links. If it contains other zips, binaries, etc, the original format is maintained.

All these actions are logged. I engage with Skitch, a screenshot type app, which I've also integrated logging for and created "cron" ( Launch Items in my case ) actions to clean up the mess Skitch leaves behind. I don't use Skitch as an image storage app, so it keeping multiple copies of everything only ads confusion.

It's pretty handy. If I want to send anything to anyone, I just find it, drop it on an app in my dock, it's 99% bash, the rest is an app that is made to take a shell script and give you same basic UI controls to make a pseudo app.

I started to have tons of link rot on DropBox. Screenshots to CSS questions that I would see posted by others but the screenshots were long since deleted.

My ~/DropBox/Public/drops/date-stamp/the-files.{html, htm, CSS, jpg, gif, png, tif, eps…etc. } directory has been filling up from this droplet for two years now. I think I have about 500MB of stuff that will forever resolve.

I do remove huge files via a "find" command that looks for specific things that I would not want in DropBox beyond a certain date or that I know were meant for specific people and the file will never be needed again. Sort of how I do IMAP image attachment maintenance in gmail but have to use a desktop app to remove attachments.