Thanks for pointing out my miss. I updated my signature, but for the thread here am on Home Designer Pro 2021 running on a Mac Pro tower (macOS Big Sur).
I have been using the help system and searching the forum, but nothing seems to be related to my issue. I started with this link from help to build a gambrel roof (https://www.homedesignersoftware.com/support/article/KB-00359/automatically-building-the-basic-roof-styles.html), which worked initially, but as mentioned not anymore. I have followed all of the steps as laid out in that link (e.g. all walls are set as hip or full gable, settings of pitch, etc.), and I do check the rebuild roof as auto rebuild is off. My thought was perhaps something should be reset entirely (i.e. cache, default setting, etc.), but I cannot seem to find anything.
I have included a few screenshots if it helps. Thank you in advance.