Everything else being equal, if we’re comparing the 2025 positions of the 2005 Buyers with the 2005 Renters I can tell you which group will have the significant advantage.
The people who bought and held in 1989 didn’t break even until 1998 or so. The people who bought in 1996 are practically bulletproof, not to mention the advantages they enjoyed as a result of their lower expense basis from 1990-1996.
The bottom line here is that if we’re talking strictly about the money then the goal isn’t to congratulate ourselves for breaking even. It’s still true that you mostly make your money when you buy.
Cashman’s situation is a little different only because he pulled the plug too early in relation to his market. Los Angeles County wasn’t (and still isn’t) on the same clock as SD County. He wouldn’t be talking about losing the difference between the rents he’s paid vs. the combination of mortgage payments he would have paid + lost equity had he held on a little longer.