As someone who has worked in South SF for years, it is pretty bad for employees. It is a cultural wasteland with few restaurants or interesting things to do. Transit is also poor as both BART and Caltrain are in awkward locations. And the fog is worse. This will be like Uber’s move to Oakland, which got rolled back pretty quickly
There is no reason why SSF couldn't be a thriving, cool place to live and work. It takes companies like Stripe to take the lead and have a vision.
Right now downtown SSF is totally boring but add a good grocery store (ahem, Berkeley Bowl) a couple cool coffee shops, wine bars and great restaurants and it would be a perfect fine place to live and work - half way between the south bay and SF.
Buy, renovate or build a place or open a restaurant in SSF now while you have than chance. It will be corporate, funky but potentially cool in 5 years with your creative and financial energy in it.