I also relied heavily on the appraisal report as a 3rd party verification that all information was accurately presented to me. 

You need an independent third party to act as QI. 

In my experience the real challenging part is to find a property that will cashflow after the refi.

The selling option on a short term property, for me, is paramount to going to the casino. 

IT's a total party here. 

You're off to an amazing start, the hardest part is securing that first deal and it seems you are on your way congrats!

However, the hard part is the expensive bay area entry price - even with the VA loan, it's still difficult to find places that makes sense for both while we house hack and when it's turned into investment property if we move.

You need to get it on your local MLS, which then feeds to all third party sites like Zillow, Trulia, Redfin, Realtor, etc.

It's now been 17 days since the sale, we're three days away from the deadline, the email thread with all parties keeps getting longer, but the situation is still not resolved.

Short term is managing cleaners, dealing with guests complaining about cleaners, random **** breaking, reporting damages do Airbnb, seeing a big *** party starting at your house at midnight (your property manager isn’t on call 24/7 and are charging for every hour spent), dealing with pissed off neighbors etc.You need to weigh all those costs (management + cleaners stack) minus potential high weekday vacancy minus Airbnb’s rising fees and declining service plus your time and headache spent, VS an easy / much more guaranteed paycheck.There’s a lot of guru BS in the STR game.