Time to sell for max appreciation in Bay Area?

[Jack Hou]

Hey all!

First time post but I have been following BP for quite some time. I'm facing this dilemma of whether or not I should hold on to my million dollar, unrealistically tiny town house. Here's the situation:  

Situation

Own a townhouse since 2016, in the booming silicon valley town - Sunnyvale. Mortgage is 90% paid off. Seen the peak appreciation 2 years ago where my gain would be close to 40%, now it's came down to 30-ish% and dropping. The property was meant to attract young tech workers with <1 kids, however given the new COVID remote work situation there seems to be less need to live "close" to work

Strategy 

The play has always been holding it and generate cash flow once as we move out to a larger space and better school house in 2021. Was betting on the continue tech growth in the area for future appreciation as well. I have a full time job so my effort in RE is always somewhat secondary / passive, not looking at strategy as sell it and obtain 3 BRRR.

Questions

- Do you guys see the housing price in bay area evens out with the remote work future? Understand this can be total opinion but it's ok.

- Is sell now the best way to maximize the gain? Or would you recommend holding and generating cash flow as everything in the bay area seem to have generous return long term. 

- What's your play for the next 6 - 18 months? Banking on the dip and enter the market? Would love to hear some thoughts! 

Appreciate the feedback and looking forward to the discussion!