It might at least make sense to group several images; if I'm trying to show someone a series of screenshots (e.g., "I click login, and then I see this, but then I click on the dancing banana, and suddenly this!") it would be easier to send a single url.
the limit is 1mb due to app engine blobfield limitations and my budget :) 1mb is enough to be useful.
I was wondering about resizing images above 1mb to fit the 1mb automatically.
Yes thumbs are a must.
Provide a browser plugin/native app/something so that I can get screenshots onto a remote serve painlessly. I hate the whole printscreen-photoshop-paste-save-upload cycle.