@Nathan Deutsch Welcome TO BiggerPockets If you are not comfy with privacy issues while house hackingyou can try  a  FHA loan or start with a partnership to buy a STR etc

I would personally use some of that equity and get started with your first property.

Putting 10%+ down with a different lender and getting lower points and interest is 100% better.

In decades past, carriers were allowing people to carrier lower limits of insurance on their properties. 

I started my career as a commercial banker a long time ago, but have been an independent mortgage broker for nearly a decade.

The 7 isles project hasn't even started.

Make the place nicer or lower the price to get bargain shoppers. 

Any advice on how to get the process started would be appreciated. 

Shouldn’t it be at a lower multiple?”

The lessons you learned the hard way in 2008 will be invaluable now, and it’s great that you’re aiming to stay small-scale and within your comfort zone of Sacramento, which gives you an advantage of knowledge in that market.Given your experience, I'd say start by focusing on three key areas to build confidence and minimize risks:Budget Control: Over-renovating was one of the big mistakes you mentioned.