It might be possible to be more contrarian when buying stock than real estate because buying stock can be more private. If your friends and family are unaware of your contrarian move, you might face less resistance. Buying real estate is publicly recorded and more difficult to hide from your family and friends. When being contrarian with real estate be ready for disagreements with your family and friends. Even though it's none of their business, they will let you know that it's a bad idea. They do this because they care about you and they mean well, but ultimately it's mostly bad advice.
When trying to be contrarian from an efficient market hypothesis, you are betting against the rest of the market, correct? That is how I see it. However, in practical terms, it's very difficult to be contrarian among your social network of family and friends. Your social network is going to be the most influential and that part will be the most difficult to go in a different direction. If your social network is deciding to be contrarian with you and going against the larger market, it's an easier decision to make because you have the support of family and friends to be contrarian against the larger market. However, when your social network is consistent with the larger market and you decide to go against your social network, that one is hard.
All four of my real estate purchases were contrarian in different ways.
House #1 was contrarian because of timing and it was a foreclosure that needed cosmetic work. I purchased in May 2007. The economy was becoming unstable, real estate sales slowed and the consensus was "wait and see." House was originally listed for 228K in October 2006 and the bank lowered the price 10K/month. When it hit 178K, my offer was 182K and I got it. I put 10K worth of work into it and it was worth about 210K after repairs. I had 3 roommates that covered the mortgage. I lived for free for my remaining 4 years of grad school. It's now worth 525K and market rent is around $3000/month. Original PITI was $1040/month in 2007 and then lowered to $940/month in 2009 with a re-fi.
House #2 was the biggest contrarian move I ever made. I got a house under contract in Fort Myers, FL in 95K in October 2011 and closed in January 2012. The house was previously worth about 250K in 2006. This was not scary at all for me because the price point was low and the location was great. However, this purchased had the loudest opposition from my social network. The reasoning for this was because the prices of these houses dropped from 250K to 100K in about 5 years. To the average person, this is scary and it means "don't buy because I'm scared." To me it was, "this is a great deal, pull the trigger." Today it's worth about 375K and market rents are $2700/month. Original PITI was $685/month.
House #3 was contrarian because it was "too expensive" among my social circle. From a national perspective, many people thought the housing market was now fully recovered and had no room to increase, so real estate moves were considered more risky due to limited upside. I purchased in June 2018 in Koloa, HI for 603K and it needed about 50K worth of work. It's now worth about 1.3 million and rents for $6200/month. Original PITI was $2700/month. It's now $3150/month due to increases in taxes and insurance.
House #4 was contrarian because the median house price for the neighborhood was 240K and I bought for 280K. I honestly didn't have much resistance from family and friends during the process. However, after I bought, many co-workers went out of their way to let me know that I "over-paid" because my purchase price of 280K was higher than the median of 240K. However, in my opinion, I didn't overpay. I actually got a deal because the seller missed the summer selling season. He listed in September 2019 and I closed in November 2019. If he listed in May 2019, he would have got 300K for the house due to more buyers in the summer. The seller was a contractor and he did an 11-month flip. His wife is a physician and he flips houses as a hobby. He doesn't really need the money. It's now worth about 400K.
When you make contrarian moves against your family and friends and end up being correct, your world becomes lonely. Your family and friends will not rally behind you and celebrate you. Even though you were correct, your resistance to the social pressure will create social fractures. This point was beautifully illustrated in the movie, "The Big Short". At the end of the movie, even though Michael Burry made money for himself and his investors, he decided to close the fund because his relationships suffered. Another point beautifully illustrated in the movie is that after his massive success with shorting the housing market, he then wanted to buy stock in 2010. He immediately got resistance from his partner because the stock market was too low and tanking. Once you have success being contrarian, nothing will change. When you go to make another contrarian move, your social network will not give you the benefit of the doubt. They will give you the same resistance they did the first time. People can't help themselves.