So, I should say that out of the GOG box, Redguard didn't want to work at all on my system. It would load DOSBox, then the black screen with a blinking cursor, and then nothing and a CTD, which I've seen reported here on the forum before. Google brought me to this guide, which I followed and used to successfully start the game, and with seemingly decent performance to boot.

However. Once I got past that opening/tutorial section on the ship with the two pirates, the game now consistently crashes while trying to load the next area. Loading takes forever (especially since it's installed on an SSD), eventually staggers its way to 50%, and then bam, desktop again. Happens every time I've tried it.

Anyone have any ideas, or should I just call it a wash?

Solved! thanks to the [url=https://www.pcgamingwiki.com/wiki/The_Elder_Scrolls_Adventures:_Redguard#Run_in_DOSBox]PCGamingWiki[/url]. In the dosbox_redguard.conf file, I just had to increase the memsize from the default of 31 to 63. Performance is a little framey, but livable. And at least it loads.