I recently started a new game with pre-existing property (House mod as I've built all 3 heathfire houses in different playthroughs & wanted to try something different).. My initial reason was that, I inherited the deed to the property in Skyrim from one of my recently departed kin. Upon my untimely arrival to Skyrim I was captured & sent to Helgen as I was associated with Ulfric.

While this works, its kind of a generic setting. How else could one come to possess said property? I'm also trying to avoid nobility. I like all of my characters to have the "Rags to Riches" theme lol.

What ideas have you used in the past?

Conquest works. I really like Valtheim Keep for instance, so mod in some safe storage, then in-game dispose of the bandits and move in. Respawning bandits simply represent others trying to dispose of the PC to move in, eh?