Jackie place offers the perfect view but the climb to her place is quite steep so if you've issues with walking or if you're traveling with a child, it might not be ideal. Jackie is communicative. She arranged for a pick up for us from the airport and also the drop back since the public transport from Oia is not very good. You'll need to take the bus to go to other places which is from the central square which is a ten min climb from Jackie's place.
Also, opting for this place in winter like we did might not be the most ideal. I'd recommend staying in Fira if you're traveling in winter and I wish someone had told us that.
I'm sure that in summer, it's much different