I managed to work around the issue for now. I manually downloaded the 5E .hl file from the wolflair site and imported it. That allowed me to load the 5e content and get passed the infinite "looking for updates". I did the same for the community pack by going here:
http://www.shadowsoftware.net/herolab/5e/ and downloading the .hl file (oddly it seems to be 1.4 not 1.5 which I got on my iPad) and importing it. I opened one of my portfolios and it seemed ok, but I haven't checked it completely.