One character has everything and still wants more. And I built those Hearthfire houses five times for him so was determined to try to get the best possible.
One character has all the player homes, never bothered with the faction stuff other than Dawnguard, and never liked the Fort anyway.
One character has Breezehome and Lakeview and will probably acquire another at some point.
One character on the PS3 is just starting out on her quest to be a land baron, she also has Breezehome and Lakeview, and is saving up her gold and iron for the rest.
Two of my four characters are home decorators, and never settle in one spot anyway, every house they own is their home. Any new characters will probably just want a house to hang up their spare set of armor.