@Account Closed, thanks for your replies and feedback.
Just some additional info - we bought the home 7-8 years ago. The calculator shows the numbers based on the current Zillow estimate, and the downpayment is based on my remaining mortgage. Based on a very cursory online search, our Campbell/WestSanJose area has 3-bed/2-bath rentals for around $3500-$3600. However, given we are already at the end of summer when schools have already started, I assumed I would be ~ $200 cheaper. However, I will be cash flow negative regardless even if I get $3700.
Another comparison I checked out is the Case-Schiller SF Home price index vs the S&P over a the longest period I could find, the comparison is shown below:
This is why I am concerned about letting it for rent.
Separately, pver the weekend, I spoke to a few realtors and it seems like the market has been pretty sluggish, and most buyers are making offers at/below the asking price, or with contingencies. Most realtors I spoke to suggested that I wait till early spring next year to sell.
This decision is too confusing :(