Photo size/orientation

I am unaware of the correct software/computer lingo involved to fix our problem but i do know some other construction software's have mastered the photo upload download capability. Currently you can only upload a certain amount of photos at a time depending on size. The system just cuts you off so if you aren't paying attention you have no idea what made it in or night. When photos are entered that were taken on a mobile device the get turned 90 degrees in the photo album but if you open a photo it "rights itself" but only while you have it open, why would that be? Conversely when we download photos to compile a weekly report 4 per page make the photo to small to view, and if we select more than a few photos our complied pdf becomes too large to send via email. There needs to be an auto compress working in the background to help with this. it is extremely inefficient for our team and frustrating for our clients.