At least in the Bay Area, Zillow et al. are decent for getting a decently accurate ballpark figure in mind. A lot of sale prices are clearly put up below market to grab attention, knowing that the sale price is very likely to exceed it by a wide margin. Here in many parts of the Bay, you'll get laughed at and promptly ignored if you try and use these "zestimates" to try and put downward pressure on the price. Sellers…
A friend was looking at houses via Redfin. The agent told him on day 1 that he should expect to spend 10%–20% more than the online quote, as a rule of thumb. Since then I've taken "Zestimates" with ~65,000 to 100,000 grains of salt.
Regarding the rule of thumb you mentioned, my wife and I have been looking for a house in the Bay Area, and we've determined that the listing price is just a completely made up number. We made an offer on a house that was 100K over asking price, and the sellers countered with 40K on top of that (so 140K over asking). I was like... what? You listed for X, we offered X+100K, you don't get to counter that. lol
We obviously didn't get the house, and they wound up selling for 175K over asking price (+~25%). We've made several other offers, and sometimes the house goes for 50K over asking and sometimes it goes for 250K over asking. It just seems to be totally random. It's absurd. Instead, we actually rely a lot on the Zestimate and Redfin's estimate to figure out what the "real" value of the house is. Z and R tend to be roughly in the right ballpark for the Bay Area.