Fastest way to get picture from iOS camera to desktop "file upload" dialog?
If you enabled photo stream on iPhone and have iPhoto/Aperture on your mac, you can try enabling photo stream on mac. If you didn't install iPhoto/Aperture,  maybe you can try MyPhotoStream.
I strongly recommend flick., which is really easy to use and covered all platforms. It's free and cool!
Share to iMessage and send to yourself after taking the photo if your iMessage on iPhone is synced with mac.




the geeky way: If your iPad has been jailbreaked, try sshfs in Mac's homebrew. Assume that you have installed homebrew and got root privilege of iPad. Just type 


  brew install sshfs


in Mac's terminal, and then


  mkdir /Volumes/iPad  &amp;&amp; ln -s /Volumes/iPad ~/Documents/iPad &amp;&amp; sshfs root@youripad:/var/mobile/Media/DCIM/100APPLE /Volumes/iPad


(I tried to directly mkdir in Documents and mount iPad's photo directory there but failed. It just didn't appear in the open_file_dialog.)

Last, just choose the photos you want from the open_file_dialog->Documents->iPad. 

If you want to unmount your iPad from mac, type


  umount /Volumes/iPad


in your terminal.

Enjoy!