First the fine print. I don't have a lot of money, nor a lot of knowledge or understanding about finance or business. I have been reading more to increase my knowledge.
Real estate. (I read the comments thus far and agree with you; I would not invest in the Bay area.) From the professionals, I hear "look at 100 deals, buy one." So, in your situation, I might look for housing in nearby states. There is a lot of investment in the Seattle area, which means that the surrounding suburbs will also get a bump. I would look for similar situations in nearby areas, and start making a habit of attending open houses to get an idea of the deals to be had. It's experience of evaluating deals which is going to increase your confidence.
I would not make it a huge thing. I think after you've seen 10-20 houses, you'll get an idea of which houses/deals you should get more details about.
Investing in the Market.
"You Can Be A Stock Market Genius" by Joel Greenblatt. Written in mostly English (meaning so laypeople can understand). Talks about how to take advantage of certain stock market events. I think following the tips in the book will increase your confidence.
"One Up One Wall Street" by Peter Lynch. Again, written for laypeople. Recommend reading; unsure I recommend buying it. Reading this increased my knowledge and confidence, but it's not the kind of book that I keep going back to.
https://armstrongeconomics.com. Martin Armstrong is someone consulted by governments and corporations to help them manage their financial concerns. He has a lot of information on his site about money, finance and economics (which I'm beginning to understand are very different things). His site is not so much for laypeople. Still, if you want a better sense of how the pieces fit into the whole, I recommend deep delving into the content on his site.
https://capitalistexploits.at/. This guy has a blog and podcast and sells an insider service. It's not cheap (for me), but it may be for you. From what I've read of his blog and heard on his podcasts, I get the feeling that you might find his services useful. What I notice about him is that he seems to be looking very long-term, world-wide, doing his research and thinking through things in a way I don't hear from many touting financial services. This guy's style is a teacher. You might not be hands-off, but have enough hand-holding such that you aren't adding too much complexity to life.
Investing in Businesses.
Know very little about this, and this might be too complex for your goals.
If you do, I would follow the real estate rule of looking at 100 business for each one you invest in.
Talking to Finance people.
I get the feeling you are talking to people about buying their services. Suggest learning more differently. For those people you find who have a passion for it, invite them for coffee or lunch and let them talk. I think you'll learn more from them than you ever will from a sales pitch.
David Bowie said that when he first started, he wanted nothing to do with the money side of music because he felt like it would be too distracting. Then, I guess after a few mishaps, he took control and started to learn about it and realized that it was a lot less distracting and incredibly beneficial to understand the financial side.
It's a game created by Robert Kiyosaki. There are definitely people in your area who meet up regularly (check meetup.com) to play the game. You will find some people there passionate about finance (or at least interested). You'll learn quite a bit. One thing I learned while playing the game with others was to not only look at the numbers for the deal, but to read the card and understand what the details of the deal were telling me. These are the same details you'll encounter in real life.