Even rewriting the URLs using DBSEO or VBSEO doesn't help. Facebook knows it's not a "real" link somehow (likely because of the redirect involved) and just doesn't use it. I've tried for months, feel free to keep trying, but ultimately it is of my opinion attachments will simply never work with Facebook.
As for the Google issue, I can't imagine any way to specify which would be the first image for every single thread on your site.
The first image will be the first image using [IMG] in a post on the page, you could add an image to the first post using an [IMG] tag to force it to be the first one created by the mod. Maybe created a custom BB Code to hide the image using CSS display:none so regular users don't even see it, but seems like a lot more work to me then it is worth.
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