Will either the LoPy or the expansion board be damaged is the LoPy is connected the wrong way? I've noticed the sticker is on upside down compared to the images and I had to match up the components to make sure it was plugged in the correct way.
Yes, the sticker is upside down on my LoPy as well. As a consequence I did mount it the wrong way first time but it survived. If in doubt, match the pins on your LoPy with the pins on the extension board. PIN layouts for the extension board can be found here: https://github.com/wipy/wipy/blob/master/docs/User_manual_exp_board.pdf
The led and push button end of the LoPy should be at the micros usb connector end of the expansion board.