I own all of them, the five we buy, and I have the mages quarters, the room in the Dawnstar sanctuary, and Kodlak's old room with the Companions. Those thieves in Riften never offered me any nice accommodation, and even the Nightingales were pretty miserable, not even a room. And Skyhaven Temple did not seem that appealing.

The five owned houses are all stocked but I am still slowly redecorating. My characters know nothing of role playing, they want it ALL! The second only has the 5 owned homes not being that interested in chasing endless quests, or being chased by endless dragons. The third character is a tad poor still and at level 10 could only afford Breezehome, but he will get there eventually.