The biggest challenge was to remember that the home was not a permanent residence, but an incoming producing property.

Do as  joe says and base it on a known price it already produces  

-Private Equity/ Venture Capital: Investing in PE is not for all as they are not simple to find and understand but for the sophisticated (and wealthy) investor you can get into some great PE funds that can produce some huge returns!

Even house hacking in LA is not going to produce cash flow. 

As for the next few years, my boyfriend and I would like to be financially free (i.e. no debt, income producing assets providing a more than comfortable lifestyle), most likely living in Southern California, with a cabin in the Rockies and another home in D.C., traveling half the year and living our absolute best lives!

If you eventually see yourself as a loan officer working locally in your market then I would try to find a top producing loan officer and work as his/her assistant.

I feel like:1) Working only with investors would produce a consistent amount of business, as many investors buy and sell multiple times in a 1 year time-frame. 2) Investors are always buying, especially when the market turns, therefore helping me stay resilient through tough economic times. 3) Incredible connections when the time comes for me to start investing.

So I just assumed refinancing would come easy...What financial institution wouldn’t want to refinance a property that is owned free and clear with a long-term tenant that is producing solid cash flow?

It should be obvious if there is a likelihood of icicle damage.A properly insulated/ventilated roof will never produce icicles.

@Franklin Marte So, in theory, commercial properties like a 9-unit multifamily would be valued based on the income stream they produce...mainly, your Net Operating Income...makes it pretty easy to determine value.