2. You can choose whichever image size you want, but if you care about the visuals and what 'looks good', it sometimes means odd image sizes. I presume there are scripts out there that minimize the image to the desired size, or crop it, like for example on Facebook's main Timeline page, where there's a background image that expands when you go over it. As you want the stories to go up as fast as possible, it is best to rely upon an automatic script.
For stories that do not have pictures, or would only have pictures later on, you would use general images according to their category - i.e. Smiths related, shows, interviews, etc.
3. As for the module at the right of the page. Yes of course it would have a caption and a link to the relevant story. You can pick any theme you fancy.
I suggested random stories/pictures from the last month, because all you would have to do is put the pictures in one folder. I don't think cropping is less of an issue with the right pane module.
I acknowledge that commercial sites have staff, but I am sure there are automatic scripts out there that can resize and/or crop images on the fly, perhaps the outcome would not always be ideal being automatic and all, but it would mean less time and effort. I'm sure bigger sites use automatic tools as well - ready made templates or macros in Photoshop to crop the images to their site's needs. As it's important for you to get the story up, it would slow things down if you would have to rely on another person and wait for him or her to do their thing. It doesn't mean a lot of work, because there aren't too many stories in a week, like the NY Times has to deal with and some of the stories are would use generic images and would be already prepeard.
So I think it boils down to finding the right script for the site, or for cropping images to a predetermined size offline and on the fly - I can look around. If you want people to give their opinion on this look beforehand, that's fine by me.