I've attached an approximation of the parts I'm working with.

I need to mate the board into the sockets in such a way that when I change the distance mates, I can determine if there is interference between the board and the connectors.  One direction was pretty simple, but the customer's application has them connectors offset in two directions, causing me a compound angle headache.  The board is a PCB and does not bend very well.

Any ideas?