Hey Stephanie,
I'm actually in a similar position - I've had long-debated dilemmas whether to continue in tech (W-2) or Real Estate (self-employed). Unless you decide to work in a large corporate mortgage company, you would have to start from the bottom. I'm sure the soft skills you developed as a PM can be transferrable, but it will require a lot of learning at the start.
I recently started as a loan officer in a mortgage broker, and there's 2 things I love:
1. Ability to directly help people and create win-win scenarios - as a lender, you can really help those in need (people with ballooning payments, difficult transactions, unconventional backgrounds) and help both professional and first time buyers.
2. Ability to see other people's deals - if you're an investor, seeing where, how and why someone is investing is a significant benefit. As a lender, you get to see the exact process they use to invest. Additionally, cultivating knowledge about different loan products will definitely help when you want to invest.
Lastly, an important point to keep in mind is the company you are working with. Surrounding yourself with people with similar goals that are willing to help you make a huge difference. Some brokers will answer every question and push you to the best, while other may take a different approach.