Chris, I feel your pain. I live in the SF Bay Area and have had an incredibly hard time getting started. It took me a long time to save up for an adequate down payment but just recently bought a place and am house hacking it because it's the only way that it works for me. Here's a quick list of a few things I did that made it more affordable and ultimately made it possible for me.
1. Look for FHA loans because their down payment percentage is so much smaller than the typical 20% route. Since a 20% down payment out here is sizable, this opened up a lot of possibilities for me once I realized that I didn't have to drain all of my accounts just to make it work..
2. Like Logan mentioned, I found an agent who specialized in investing and house hacking. It was actually David Greene's outfit since he's local and it worked out very well. My agent targeted properties that I was interested in (mostly du-tri-quad-plexes so I could house hack) and ran quick numbers to make sure it would pencil out before they would even show me a place.
3. House hacking is the biggest reason it worked for me because it would be tough for me to afford the mortgage all on my own. I bought a SFR home with an ADU in the back, and I live in the ADY and rent out the main house which is 3 bed/2 bath. That pays for a huge chunk of my mortgage and allows me to save up money for my reserves and strategize for the next place that I want to buy.
It seems like you listen to the podcast regularly so you probably know much of what I laid out, but hopefully some of it was helpful.