Selling your primary residence to finance investments?

[David Mazza]

First post, need advice! I’ve been in CA all my life and “lucked” my way through real estate by living in my flips and moving up the property ladder. I’m at a point now where I have a condo in SF (bad economics on a rental basis but solid appreciation by accident) and a primary residence on the Peninsula that has cash tied up. I’m thinking of selling it all to get started on more strategic investing to get towards this mythical path of financial freedom, but that may involve moving the family into a rental for a bit. Has anybody journeyed down this path before? Any advice? How afraid of losing the tax write off of a primary should I be? I’m new and appreciate any and every response!