It may be an issue with the potting medium, most of which break down and become too compact over time, creating drainage issues. I'd ask on the container gardening forum.

There are two ways I know of getting your photos right side up in GW. One is to figure out what way you have to position the camera or phone in order that the photo is upright. For instance, with my phone, the button I push to take the photo has to be on the right with the phone held in landscape mode. Mostly though, I just pop photos into image processing software and rotate it and then save it. My image processing software was a freebee with the computer, but I imagine that there are free apps as well.