.: Decided to try to use Obie on a new acquisition because my traditional insurance doesn’t do new policies in California and the insurance agent recommended by my loan officer just wasn’t working fast enough (CA Fair Plan seems to be at fault) to meet our closing calendar. 

It depends on what your plans for the property are. 

I will suggest you plan to House Hack a Duplex or Triplex or Fourplex every year for the next 4 to 5 years and you will thank me later.Goodluck man and keep us posted on your progress!

First floor has a newer furnace (2016), two units upstairs share one furnace.  

If you are not coming in cash and you plan to hold for five or more years, its the best time to pick up a property at a steep discount and make it work until the cycle turns again.  

We've got great reviews and super host status on a personal account, but we're planning on building a brand via our management company and buying cabin communities / boutique hotels as well.

You sell when it fits with your original business plan (targeted NOI is reached, timeline is reached, etc.). 3.

At a minimum,  you should understand what the current zoning is and what restrictions there are.As the post above mentioned reaching out or going in person to speak with the planning and zoning department will be very helpful. 

Dmitri then called the 10K an "onboarding fee" as a means of justifying why the fee would have to come first and reiterated that it would be 10K up front for every property I might want to purchase (if my intent was to purchase 2 properties it would be 20K up front, and if my plan was to buy 5, then it would be 50K up front). 

I'm not talking about cosmetic fixes, I'm talking adding bedrooms within an existing floor plan, creating a second unit (like an ADU), etc.