All in all, the STRs are contributing to the affordable housing issue but there is much more at play, at least in our local environment.

I’d then like to rent out the multifamily and leverage, if possible, the equity from that investment property into our SF primary residence.From what reading I have done it seems the consensus is to not wait for the market to invest, but does this apply to a primary residence as well (what about a potential bubble environment, maybe another post required…)?

@Daljit Singh try out www.steve-rich.com  Steve Rich environment.

If you want to make sure the roof will be fixed stand by at the Open House and tell every buyer they have a roof issue lol - that's one way of competing in this crazy environment. 

I suspect we are going into high inflation environment with rising rates so it will likely go up over time. 

Get comfortable in the environment first,...then get involved in it.

The inflationary environment alone is a compelling reason to own or have ownership interests in real assets. 

Especially in todays environment. 

If you are concerned of being in an estate tax environment, consider then both estate and income tax (step up basis planning).

The environment is always changing but I encourage you to try to look at the bright side and make sure you are preparing for issues but don’t that detract you from appreciating the wins.