Are you able to provide your routing? There are some 3rd region routing rules that prevent booking as one award, and when one tries to price it out as a same-day multi city, the site crashes.

1: On the website, no. If not award, ITA Matrix, but can't do that for an award.
2: Yes, put the more detailed one on hold and call to add the other. I don't believe they can merge PNRs, just add to them. (This works as it's a partner award, and they can change those).