Thanks @Sam Josh for your perspective. It's very helpful. This property is a "middle of the road" property for the peninsula. My ideal would have been in Millbrae, Burlingame, or San Mateo. This new primary residence is north of those cities. To buy a modest property in those cities with better schools would be $2M+.
I feel like I'm buying at the top of the cycle, which may be fine since there is never a good time to buy. I thought I was buying at the top 11 years ago and now see $300k appreciation on my current home. If I buy the new home, I have the option to rent it out for a good cash flow, or sell it at what I think is a top and invest in a 10 unit with ~$10k gross income a month in CA ($20k in some parts of the country. I have to find those!)
@Amit M. a house down the block just accepted an offer for $1.6M-$1.7M. In 2 years, there is a lot of new development coming available. There are at least 570 units in South San Francisco planned. San Bruno and Millbrae also have a substantial amount of new developments currently in the planning process and could be coming available in 2 years.
Supply risks are something I'm considering. The new units coming in are condos, townhomes, and SFH. I'm also considering the increased population pressure on the school district where my kids will be attending. If the new developments offer the same size and floor plans, they may lower the value of my home if they are offered at a lower price.
Interest rate risk is also a risk. As interest rates are climbing, I should lock in my primary residence at a lower rate for the long term, albeit, higher price. If there is a price correction (an aggressive 25%) because interest rates are climbing, the monthly payments wouldn't be manageable at another $1.5M property.
Assuming 2% appreciation in the bay area's peninsula, my $1.525M purchase is $1.586 in 2 years. That's ignoring the increase from $1.525M to $1.65M. If I start with a $1.65M value assumption from the offer the seller already received and the offer a home down the street received, in 2 years, the home could be worth $1.7M.
I think the best course of action is to purchase the "modest" $1.525M house, sell my current property, and buy an investment property with the $400k gains. This would make my family very happy. Kids would be able to have more room to run and play. Neighborhood has many kids the same age as my kids and the parents are friendly.
On the flip side, we are cozy where we are. We are currently saving ~50% of our income. We could live off my wife's income if I choose to devote my time to real estate and quit my job today. I want to keep a W-2 job so I can continue to invest in properties, whose cash flow will equal $10k/mo.
The former will delay my goals, but will make my family happy now, and also make me happy. The latter will make me happy in the future, and fairly invisible to my family.