05/29/2026
A while back, we were lucky to have Richard Bailey, former Mayor of Coronado in San Diego, and now running for City Council, on the podcast.
We spoke about many things, including the burden of the middle class in San Diego.
It feels like the middle class is carrying the heaviest burden in San Diego right now.
On one end, you have higher-income households that can still afford rising home prices, coastal communities, and the increasing costs that come with living here.
On the other end, there are individuals and families who may qualify for assistance programs, subsidized housing opportunities, or other forms of support.
But for many people in the middle, there’s no safety net—and no easy path forward.
Richard said he had recently had someone reach out and say something that perfectly captured what so many San Diegans are feeling:
“I make too much to qualify for help, and I make too little to get ahead.”
That’s a tough place to be.
When housing costs continue to rise and additional expenses like parking fees, trash fees, insurance costs, and everyday living expenses keep piling on, it’s understandable why some people start asking a difficult question:
“Can I realistically afford to stay here long term?”
San Diego is an incredible place to live, but affordability continues to be one of the biggest challenges facing local residents. Understanding the market, knowing your options, and having a plan is more important than ever.
Daniel Fefferman | CA DRE 02026109 | Broker-Associate | Founder
Jessica Speciale | CA DRE 02082038 | Realtor