In general home ownership is less useful for single guys without kids. One huge perk of being a single guy without kids is if a job opportunity pops up in Seattle or San Francisco or Tokyo you can pick up and go. Buying a place can limit that.
The big perk would be if you are renting for $3,000 a month and can find a place to buy where your mortgage and taxes are less than that, you can potentially free up cash every month. And there are tax benefits for the mortgage deduction, and that single guy making six figures isn’t getting the same deductions those of us with kids get.
I have no clue where housing prices are going to go. All of Rich’s data suggests there is little supply to drive down prices. But the fundamentals seem rather poor if you look at incomes vs. prices. I guess if you go in expecting no appreciation and only look at tax benefits and a mortgage less than current rent it might be a fairly safe bet?