WHOOOO HOOOOOOO, I figured it out.
I spent time looking at the weird not parsing slashes issue. I started looking at the db tables, went into the settings table and found a path w/o slashes - it's the Orignial "Image storage directory server path" - I still have not found where to adjust this thru the forum admin, so I changed it directly in the db to match the other data url and path.
Made sure both url and relative path had a slash on the end.
Thanks for reading..