In San Francisco, when I was looking for an apartment,, I always ended up with an apartment with the worst pictures / missing things in the description on Craigslist, because they had less interest / were cheaper.
The market for rentals is never efficient and will never be! People who post to Zillow with a perfect description know they can extract more money for it.
I bought my house in the late-ish 90s before the web was really a big thing and certainly before things like Google StreetView. I spent a lot of time driving around to see places where I ended up not even stopping the car once I got there.
Today, there would be a lot more information available. However, as you suggest, I assume all that available information probably increases the efficiency of connecting a property with potential buyers/renters so you're less likely to luck into something that others just haven't found yet. (The funny thing is that the house I ended up buying turned out be being sold by someone I knew quite well at work.)
We almost didn’t stop into the house we now live in. It was #10 of 10 of open houses on a rainy Saturday and we were just looking to get a sense of things we both liked/didn’t like. This listing had terrible photos and the building had almost no updates since 1993. We walked in and in 2 minutes knew we’d want to buy the place, in part because it showed so poorly and the sellers were motivated to close. Zillow was a thing, but nowhere near as big a force as it is now.
When I saw the house I eventually bought, I had seen one property I was interested in but was on the fence about. When I saw this one I was pretty much sold. Great property. The house was old and very little had obviously been done with it for decades. And there were some things (like on the small side and one bathroom) that would probably have been showstoppers for a lot of people but weren't an issue for me.
Various things cost me a fair bit of money, effort, and angst that I'm glad I didn't know about at the time. But, at the end of the day, I got a ridiculously good deal--especially by today's standards--for a semi-rural place only about an hour out of Boston.
The worse the advertisement the better. I lived in an absolutely lovely townhouse which had no pictures posted and a description which failed to mention any of the amenities. My current house was shown with no staging and blackout curtains. They only got 3 offers in 2 weeks, in a market where most listings get t 30 offers in a week. It pays to look seriously when doing so takes more effort.
When I moved to Sunnyvale, I found a place on Craigslist where the entire description was typed in capital letters. The landlord was indeed quite eccentric, but we got along well. 2 bed 2 bath, vaulted ceilings. There was a pool that I maybe used once. It was good for 3 years, until his sister took over the family business and evicted him! Poor guy had a lot of mental health problems, but she was the insane one...
The market for rentals is never efficient and will never be! People who post to Zillow with a perfect description know they can extract more money for it.