I have only carried insurance on the house I had and my wife had before we got married.

There are certain things in life where it seems like you’ll never be 100% for sure ready like having kids getting married a major job change ,etc .. real estate is like that .

I love the Berkshires, my wife and I met at UMass and got married at Berkshire East :)  It sounds like you're thinking about things the right way, you've minimized your cost of living and you've been able to consistently save a nice little nest egg for yourself. 

The one piece of advice I will give you is marry your fiancé before you buy a house with her.

being in a Co OP I would bet dollars to donuts its SF proper or maybe Oakland.. if its owner occ she made a ton of equity she could cash out tax free. or at least 500k if she is married 250k single.. that's the best tax treatment we have in America.. then decide what she wants to do..

This is a conversation I often times have to have with individuals who are married and/or have kids... is finding that compromise that works best for them. 

My wife and I are newly married and have been doing our research and are about to get into real estate investing.We however have become torn between whether we should buy something here close to where we live in Southern California (which would be our first property and we would want to buy a duplex to house hack) or buy something out of state as our first investment to get started as it would be much cheaper. 

I'm married, have an almost 3-year-old son, and I'm incessantly focused on how I can replace my income, and become completely financially free while my kid is still young.We bought our home up in Lacey, WA, and sold it before moving back here 3 years later.

You don't pay capital gains on your personal residence up to 250k if single or 500k married. 

With you being married that'd probably tip off the bank anyway.