It looks like Ashleigh and Blaise have crossed paths professionally indeed. After reading about her, Blaise definitely knows who she is and seems to share some of her thoughts on matters. I look forward to their conversations!
Blaise was a little stuck on the notion of pureblood heritage in school, so he would not have given Bethanie much thought I'm afraid. He regrets this attitude now though and would not think less of her.
As far as Ron goes, I think Blaise would see Ron and him like fire and... a different fire. Their discussion would probably be awkward, but could be a lot of fun!
From what I've read of Andrew, Blaise would not have noticed him in school, and would not know how to handle him if he met him now - this might have potential in the future perhaps?