Stolpen (bus) OR Moritzburg (steam train from Radebeul) - both have castles - which would be more interesting?
Moritzburg is more picturesque and great for photos, but I would still recommend Königstein fortress instead.
PS: and if you visit Königstein fortress don't use the elevator but enter the fortress through the main gate, the most vulnerable part of the structure. IMHO that's the most interesting feature of the fortress.
Pirna (Sonnenstein Fortress, museum on the the Nazi euthanasia
program), OR Colditz (castle where British prisoners escaped) Which
would be more interesting?
Colditz as a castle is more impressive, and they offer more in terms of WW2 stuff. But the old town of Pirna is quite nice, and the town church has a nice interior.
If we did rent a car for the day, could we combine Meissen and Colditz
or is there a better combination?
It's possible, but keep in mind that Meissen, with the castle, the cathedral, the old town and the porcelain manufacture, will take some time, so I guess you can't see everything.
As a alternative you could combine Colditz with Saxonys most beautiful castle: Kriebstein. This area is actually full of castles.
Radebeul (wineries) OR Leipzig
Depends on your interests. For a relaxed day you could hike from the Renaissance summer house Hoflößnitz (beautiful interior) through the vineyards to Wackerbarth castle, which has a good shop. Radebeul itself is a small town with many posh villas, but there is also a old wine village called Altkötzschenbroda, which offers many cozy restaurants.
Leipzig on the other hand is a big city and feels a bit like Berlin in small. It's also called "Hypezig" because it became quite popular among hipsters...
Any thoughts would be MOST appreciated!!!
Well, I know you can't see everything, but I miss three regions in your list: Upper Lusatia, the Ore mountains, and Saxon Switzerland. To me these are the highlights of Saxony.
Upper Lusatia is the region between Dresden and the Polish border. It was part of Bohemia (todays Czech Republic) for a long time and is culturally not really Saxon. It also houses a small Slavic minority around Bautzen, the Sorbs, and in the eastern part around Görlitz you can encounter many Silesian traditions (Görlitz was part of the Prussian province of Silesia, and after WW2 Silesia fell to Poland and many of the expelled German inhabitants settled around Görlitz).
Both Bautzen and Görlitz are highly recommend. Bautzen is a Baroque town surrounded by medieval fortification and the cultural capital of the Sorbs, and Görlitz with more than 4.000 listed buildings is simply one of Germanys most beautiful towns.
The Ore mountains were once the richest part of Saxony, and the area deleveloped a very unique culture. Basically everything there is related to mining, and even in small villages you sometimes find two or three visitor mines. The mountains are moreover Germanys Christmas country, since many of the traditions were born there.
I would recommend to see at least Freiberg, a beautiful preserved miners town, once the richest town of Saxony, and if possible Seiffen, a village deep in the mountains with nothing but Christmas shops all year round.
And Saxon (and Bohemian) Switzerland is a must. These are simply the most picturesque mountains of Central Europe.