Hi @MRyan and a very warm welcome to the Community Forum and I am sorry that you are having this issue uploading your photos. Have you tried contacting Membership Services? I will also tag @Angela_L and @Carla to have a look at this issue for you.
For reference, as a member, you can also add your TrustedHousesitters profile on to your Forum profile by following the attached link, should you wish. This will then enable others to offer you helpful advice and feedback.
If you are unsure how to do this, or if you have any questions at all, do not hesitate to ask, we are all more than happy to help.
Also, remember you can use the spyglass symbol at the top of the page next to the TrustedHousesitters logo and search for any questions that you may have as they have most likely already been answered on here and of course if not then please just ask! 