Coming late to this discussion... Chris I experimented with tender succulents outside under a deck this winter and the graptoveria (which is what I think you have in the first three photos) will do fine even in extreme cold so long as they are kept on the dry side
However if you figure out a way to keep them dry in winter will it be too dry during summer? Figuring out the right drainage is an individual thing. You could also place bags or something over the plants when you know you're going to have several days of rain. I find these specific plants to be easy and forgiving! Mine sustained temps in 20s for a few weeks and are fine
Hope that helps
Pic of one planter box which did well, remember mine are on a covered deck so they are dry, they took the freezing temps with ease