I had the exact same problem with the Whiterun steward. Bought a house, didn't have enough gold for anything else. When I came back, the dialog option to buy furniture just wasn't there anymore. It reappeared a couple of play sessions (or in-game days?) later, no idea why...
That's all I've got...
It seems that you need to strike up a conversation during daytime, only when he stands near the jarl. Indeed that option isn't available otherwise, neither when he rests in his bedchamber nor spends time on the balcony.