Hmm, perhaps being the thane of said hold is essential??
To elaborate on that, I agree with another post around here, about how I really, really hope it's something you have to actually work for to get. A completely broke, fresh-off-the-wagon character shouldn't be able to be like "Hey, I just escaped Helgen and killed a few wolves. I sold their pelts, so now I can afford to buy some of your land and build a gigantic ass house."
That was, of course, an exaggeration, but I think it got my point across.