If you can get the larger condo that you want and not have to sell the current condo, I believe that would be your ideal choice right now.
For the under $300K in the 92101 there are only 2.87 months of inventory.
For the under $350K in the 92101 there are only 3.03 months of inventory.
For the under $400K in the 92101 there are only 3.59 months of inventory.
The pendulum has swung too far and prices are below values, imo
I believe the pendulum is already swinging back to normal.
You should be able to cashflow given what you owe and the potential rents (including vacancy)
Robert T. Boyer, Ph.D.