Here are my thoughts . . . well, opinions really.
Madrid is the least interesting of all your cities to visit, in large part (for me) because it doesn't have the centuries of history (sights and architecture) of all the others. Its main draw is painting - 3 top-notch museums. Note that unlike other major art museums, these collections are almost entirely paintings, medieval to modern. Madrid is also very easy to fit into just about any Spanish itinerary - it's only 2.5 hours by train to Barcelona, so I would put it aside for your next trip.
Toledo I like Cordoba marginally better and Cordoba is my favorite Spanish city. Given your limited time, it's more efficient to stay in Cordoba. Cordoba is about 3/4 of an hour less travel time by train from Madrid than Sevilla is, so I'd consider going there right at the start. It has a large, well-preserved medieval section including the Juderia, parts of the old city walls and the Mezquita. 2 nights.
Sevilla You can get door-to-door from Cordoba to Sevilla is about 1.5 hours and trains are frequent. You have the choice of spending most of your travel day in Cordoba (evening train) or getting an early start and having a nearly full day in Sevilla. You can see the main sights in 1.5 days. You could day-trip to Jerez/Arcos. The best thing in Jerez is the show at the Royal Equestrian School (around 11.00-noon, only a couple days a week). The Tio Pepe sherry bodega tour is fun. From the Jerez train station, take the bus to Arcos and explore for 1/2 day (use the RS self-guided walking tour). 3-4 nights.
Ronda Leave Sevilla in the morning and you'll have lots of time to explore the hill towns on the way to Ronda. Use your full day to see the sights in Ronda and hike down to the Gorge, or spend a few hours exploring more hill towns. Sunset's between 6-6.30 pm in November. 2 nights
Granada I would put this back on the itinerary. There's a reason it's the top sight in Spain. Also Granada is fairly difficult to fit into an itinerary because of its location. If fitting it when you are seeing nearby places isn't convenient, think how much less likely it will be to see it on your next trip to Spain. Leave Ronda early and you can hike for hours in El Torcal (near Antequera), If you aren't doing this on a Monday, stop on the way to El Torcal to see the prehistoric dolmens just outside Antequera. It's about 1.5 hours driving from Ronda, another 1.5 to Granada on mostly flat, divided highway. 2 nights.
By the way, Sevilla, Ronda and Granada also have historic medieval town centers.