Problem the first: So, I'm looking at my home page in the CMS. I want to add an image below some text. I hit the little tree image icon and upload a JPEG to assets/uploads. I select the image (I get only file names to choose from, no thumbnails), select Centered on its own, and Insert image. OK, looks good in the CMS. I save and publish. The published site has a little rectangle in Firefox and a place holding rectangle of the correct size in Safari. Viewing the source shows the HTM generated by Silverstripe has this for the image location: "assets/Uploads/_resampled/ResizedImage60070-Logo.gif". Guess what? No such file in the _resampled folder. The same thing happens with any images. If they are in a subfolder in uploads, then the HTML points to a non-existent _resampled folder within the subfolder.
Problem the second: I trashed all the images in the uploads folder to start fresh but the CMS thinks they are all still there. Rebuilt the DB, flushed everything I could think of. CMS says images are there. Try to edit one and the CMS doesn't say "no image", it crashes.
Any takers? I'm out of things to try and behind schedule. You can visit andahammer.com and view the source.