@Christopher Greci I hear you! I too am an engineer making good salary in a good company BUT I've spent over $100k in rentals over the past 4 years! So 6 months ago my wife and I both said, "enough is enough!!!".
We were living in mid peninsula and paid a premium (rentals) for the convenience of the location. Like yourself, my wife and I favor a minimalist nomadic lifestyle and we've looked at all options: building tiny homes, living in trailers, living in a boat in a marina, in a van, or even just moving around in motels.
We decided while all these are great at building experiences, it does not build financial wealth so we decided a compromise would be to "downsize" our lives into a studio that we've separated out of a 3bd 2 bath SFR that we bought as an investment and rent out the 2 bed 1 bath. House hacking if you will! Use our money towards building an asset while saving money!
The house's almost an hour north of SF so rather than treating it as a home, we use it more like a permanent motel that we go back to sleep in. So far we're pretty happy with the results; we get to socialize more, explore more, do more road trips. Right now we're considering getting a van that we can use as a second base in the peninsula. You know, for those times that we just need a private place to chill or sleep in.
We did considered renting in a rent controlled place too but found it too restricting for the kind of "pack and go" lifestyle that we want. With our back studio, we can always pack our bags and rent it out if there's a call for us to live in another city/country.
We can do this coz we're young and don't have kids... yet... I guess all these will change once they come into the equation. We figured we've a good 3 years before good schools becomes an issue so we're gearing up towards maybe purchasing or renting a great neighborhood down the line.
All the best in coming up with your own solution to your lifestyle! ;)