Deeby ~ Gotta picture? That sounds lovely.
Pineapple sage, I have found, for my area anyway, grows best in a pot or raised bed. It just doesn't like our mucky clay soil in winter.
I had one for a couple of years, and then planted it in the ground...bye, bye!
I think oregano should be in a pot for a different reason. It is like mint. It gets deep-rooted and likes to spread. I had a time digging it all out. Now I want to grow it again. I probably could plant it in an out of the way area, where it doesn't matter how wide it spreads, instead it of fussing with a pot to keep it watered. When it is in the ground, the only maintenance required is cutting back the old dried stems. It is probably deer-resistant, due to its fragrance and being in the mint family.
My rosemary plants are over 30 years old. I trim them now and then. I usually deep-water them once or twice during the summer, though I may have missed them last year.